Ammonia → HCID 19963762, compound

Temperature

0 °C

2,3-Dihydrobenzofuran-7-carboxylic acid (15.0 g, 91 mmol) was dissolved in DCM (150 ml) and DMF (150 ml). 1-Hydroxybenzotriazole (12.3 g, 91 mmol) was added. The solution was cooled to 0° C. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (17.5 g, 91 mmol) was added. The reaction mixture was stirred for 20 min at 0° C. A 1 N solution of ammonia in methanol (200 ml, 200 mmol) was added. The reaction mixture was stirred for 16 hours, while it was warming up to room temperature. It was diluted with ethyl acetate (200 ml) and washed with a 10% aqueous sodium hydrogensulphate solution. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The remaining crystals were washed with ethyl acetate (3×100 ml) and dried in vacuo to give 5.21 g of 2,3-dihydrobenzofuran-7-carboxylic acid amide.

1. stirringThe reaction mixture was stirred for 16 hours, while it
2. temperaturewas warming up to room temperature
3. washwashed with a 10% aqueous sodium hydrogensulphate solution
4. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
5. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (400 ml)
6. dry with materialdried over magnesium sulphate
7. customThe solvent was removed in vacuo
8. washThe remaining crystals were washed with ethyl acetate (3×100 ml)
9. customdried in vacuo

ORD record

ord-9cfd572191e049cea39bbd3b440bbca7

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1