6836-22-2
7-Methoxy-1-naphthaleneacetic acid
CAS: 6836-22-2
Molecular Formula: C13H12O3
6836-22-2 - Names and Identifiers
| Name | 7-Methoxy-1-naphthaleneacetic acid |
| Synonyms | 7-Methyl-1-naphthyl acetic acid (7-Methoxy-1-naphthyl)acetic acid (7-methoxy-1-naphthyl)acetic acid 7-Methoxy-1-napthalene acetic acid 7-Methoxy-1-naphthaleneacetic acid 2-(7-Methoxy-1-naphthyl)acetic Acid 1-Naphthaleneacetic acid, 7-Methoxy- (7-methoxynaphthalen-1-yl)acetic acid 2-(7-Methoxyphthalen-1-yl)acetic acid 2-(7-Methoxynaphthalen-1-yl)acetic acid |
| CAS | 6836-22-2 |
| EINECS | 1312995-182-4 |
| InChI | InChI=1/C13H12O3/c1-16-11-6-5-9-3-2-4-10(7-13(14)15)12(9)8-11/h2-6,8H,7H2,1H3,(H,14,15) |
6836-22-2 - Physico-chemical Properties
| Molecular Formula | C13H12O3 |
| Molar Mass | 216.23 |
| Density | 1.235 |
| Melting Point | 153-154 ºC |
| Boling Point | 408.8±20.0 °C(Predicted) |
| Flash Point | 160.7°C |
| Solubility | Dichloromethane (Slightly), Methanol (Slightly) |
| Vapor Presure | 2.04E-07mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 4.33±0.30(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.625 |
6836-22-2 - Reference Information
| overview | agomelatine intermediate 3 can be used to synthesize agomelatine, which was developed by Servier company and was first listed in Europe in 2009. Agomelatine is the first melatonin receptor agonist with good antidepressant effect. It has a fast onset, good curative effect on depression and its accompanying anxiety, insomnia and other symptoms, with few adverse reactions and high safety. |
| preparation | step 1. the preparation of methoxy quinone (3) in the reactor, add 6.33g(0.04mol) of 2-naphthyl ether, 200ml of dried dichloroethane, cool down to -10 ℃, drop 250ml of oxalyl chloride, then add anhydrous aluminum trichloride 10.67(0.08mol) in batches at -10 ℃, after adding, keep the temperature at -10-0 ℃ and stir for 8.5 hours, then naturally raise the temperature to the ambient temperature and stir overnight, stir the reaction liquid and pour it into a cold aqueous hydrochloric acid solution to separate the organic phase, the aqueous phase is extracted with dichloroethane, the organic phase is combined, dried by anhydrous sodium sulfate, the solvent is distilled under reduced pressure, and the remainder is recrystallized by dioxane, 7.47g was obtained with 88% yield. Step 2. (7-methoxy -1-naphthyl) preparation of oxyacetic acid (4) in the reactor, add 100g of 3-methoxy quinone, 1000ml of dimethyl sulfoxide, stir for 10 minutes, then add 18-crown -6-ether 4g and 230g of sodium amide, stir for 30 minutes at ambient temperature, then add 2000ml of water, add 3000ml of 2N hydrochloric acid solution, stir for 30 minutes, extract with ethyl acetate for two times, combine organic phases, wash with water, dry with anhydrous sodium sulfate, and evaporate the solvent under reduced pressure to obtain yellow solid with 94% purity and 88% yield, m.p.99 ℃. Step 3. (7-methoxy -1-naphthyl) acetic acid (5, agomelatine intermediate 3) is prepared in the reactor, 240ml of diethylene glycol, 130.4g of 2-(7-methoxy -1-naphthyl) oxoacetic acid and 72g of hydrazine hydrate are put into the reactor, stirred at the ambient temperature for 1 hour, added 130g of potassium hydroxide and then slowly increased the temperature, and refluxed for 3 hours when the temperature rises to 138~140 ℃, after distilled out water, the temperature increased to 180 ℃, heat preservation and reflux for 0.5 hours, and the HPLC detection reaction was complete. Cooling to 120~130 ℃, pouring 2.4L of cold water, washing out the materials in the bottle with 300ml of water, combining, filtering with 24g of diatomaceous earth, leaching with 300ml of water, adjusting pH = 1 with 600ml of hydrochloric acid (industrial hydrochloric acid: water = 1:1) for clarification mother liquor, precipitating white precipitate, cooling to 10~15 ℃, filtering, leaching with 300ml × 2 of water. Bake at 50 ℃ for 14 hours to obtain 189.6g of white powder with 95% yield. |
Last Update：2024-04-09 01:59:59
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