Methanol → 2-(4-Fluorobenzamido)-4-methoxy-3-methylbenzoic acid

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Water	HCID 962	—
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	2-(4-Fluorobenzoylamino)-4-methoxy-3-methyl-benzoic acid methyl ester	HCID 59165419	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-(4-Fluorobenzamido)-4-methoxy-3-methylbenzoic acid	HCID 59165475	101.4%

Reaction Conditions

Temperature	50 °C

Reaction Steps

LiOH (1M, 4 mL) was added to a solution of 2-(4-fluoro-benzoylamino)-4-methoxy-3-methyl-benzoic acid methyl ester (65) (870 mg, 2.7 mmol), in tetrahydrofuran (15 ml), water (7.5 ml) and methanol (7.5 ml). The mixture was heated to 50° C. for 4 h. Water (30 ml) was then added and the volume reduced to half. Acidification with acetic acid followed by filtration gave pure title compound (830 mg, 100%). MS (M+H+) 304.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07989471B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-40122db84b2748a38b43bac14f3511e1
Source note	uspto-grants-2011_08