2486-69-3 → 4-Amino-3-methoxy-N-methylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	2486-69-3	HCID 288057	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Methylamine hydrochloride	HCID 6364545	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Product	4-Amino-3-methoxy-N-methylbenzamide	HCID 20444434	63%

Reaction Steps

To a solution of 4-amino-3-methoxybenzoic acid (1 equiv) in N—N-dimethylformamide (0.6 M) was added sodium bicarbonate (9.7 equiv), HATU (2 equiv) and methyl amine hydrochloride (10 equiv). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured on water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 100-200 mesh, 0-10% methanol in DCM as eluent) to give the title compound. (Yield: 63%). MS (ESI) m/z 181 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09346812B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-c0dadfb2e4c848ff9fd17ea80158f490
Source note	uspto-grants-2016_05