Methanol → 3-Chloro-4'-nitrobiphenyl-4-carboxylic acid

HRID 2356832Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].CO.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 3-chloro-4′-nitrobiphenyl-4-carboxylate (0.50 g, 1.4 mmol) was suspended in THF (6 mL), MeOH (6 mL) and water (3 mL), and NaOH (0.27 g, 6.9 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure and acidified with 2N HCl. The resulting solid was collected by filtration and dried in a 40° C. vacuum oven, yielding 0.315 g (83%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.81-8.10 (m, 5H), 8.21-8.38 (m, 2H).

Workup

temperatureUpon cooling to rt
concentrationthe reaction mixture was concentrated under reduced pressure
filtrationThe resulting solid was collected by filtration
customdried in a 40° C. vacuum oven

Sources & evidence

ORD record: ord-bbf8da09b761409ca77dd02801f32f17
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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