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ChemicalBook CAS DataBase List 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide
15992-10-6

2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide synthesis

4synthesis methods
-

Yield:15992-10-6 99%

Reaction Conditions:

Stage #1: Indomethacin amidewith sodium hydroxide;water in DMF (N,N-dimethyl-formamide) at 20; for 3 h;
Stage #2: with hydrogenchloride in DMF (N,N-dimethyl-formamide);water; pH=9;

Steps:

7

[0257] 5-methoxy-2-methyl-3-indolacetamide (Compound 303). Compound 301 (3.5 g, 9.8 mmol) was dissolved in dry DMF (100 mL) and stirred at room temperature. NaOH (10 N, 20 mL) was slowly added in small quantities over 1 hour while monitoring the reaction by TLC. The reaction was judged complete after 2 hours by TLC. The pH was lowered to 9 by the addition of HCl (4 N). DMF was evaporated via high vacuum rotovap, and syrup was taken up in ethylacetate (600 ml) and washed with sodium bicarbonate (3×300 mL). The aqueous layer was washed with ethylacetate (3×400 ml), and all organic extracts were combined, dried with sodium sulfate, and solvents removed to give 99% product.

References:

US2005/2859,2005,A1 Location in patent:Page/Page column 22