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

HRID 1669585Notes

Reaction equation

[Li+].[OH-].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH3:14])[C:7]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.O.CO>O1CCCC1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:7]2[C:8]([CH3:14])=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=2[C:5]([OH:25])=[O:4])=[O:24])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

filtrationAcidification with acetic acid followed by filtration

Sources & evidence

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

Reaction notes

Loading…