Ammonia → 2-Amino-3-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-Amino-3-methoxybenzoic acid	HCID 255720	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Amino-3-methoxybenzamide	HCID 18536571	—

Reaction Steps

To a solution of 2-amino-3-methoxy benzoic acid (5.00 g, 29.9 mmol) in THF (50 mL) were added EDCl (6.88 g, 35.9 mmol), HOBt (4.85 g, 35.9 mmol), N-methylmorpholine (3.60 g, 35.9 mmol), and aqueous ammonia (50% v/v, 30 mL). Then, the reaction mixture was stirred at room temperature for 48 hours. Then, water was added and the product was extracted with ethyl acetate (2×250 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous Na2SO4. Removal of solvent gave product 2-amino-3-methoxy-benzamide as a light orange solid. Yield: 1.70 g (34%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238640B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-83f039f79786465c8f7945b0617fcf87
Source note	uspto-grants-2016_01