2-Methoxyformanilide → 2-Methoxy-N-methylaniline

Temperature

0 °C

To a cold solution of 9.0 g of N-formyl o-anisidine in 50 mL of THF was added 66 mL of a 1M solution of LAH in THF dropwise at 0° C. After complete addition the reaction mixture was stirred at 0° C. for one h. The reaction was then quenched with ethyl acetate, then with a saturated solution of NH4Cl. The mixture was extracted with ether, the combined extracts were dried over magnesium sulfate, and the solvent was removed to give 6.0 g of product. 1H NMR (300 MHz, CDCl3) δ 2.85 (s, 3H), 3.83 (s, 3H), 4.16 (s, 1H), 6.61 (dd, 1H), 6.69 (m, 1H), 6.75 (dd, 1H), 6.87 (m, 1H).

1. additionAfter complete addition the reaction mixture
2. customThe reaction was then quenched with ethyl acetate
3. extractionThe mixture was extracted with ether
4. dry with materialthe combined extracts were dried over magnesium sulfate
5. customthe solvent was removed

ORD record

ord-3edeb1f8f104406e9367e6c6f44ecfd3

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245799B1