Methanol → Methyl 4-amino-3-nitrobenzoate

HRID 58182

Reaction equation

S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[CH3:18]O>>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:18])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 3941008Methyl 4-amino-3-nitrobenzoateYield 100%

Procedure

Thionyl chloride (19.4 g, 164.85 mmol) was added to a solution of 4-amino-3-nitrobenzoic acid (20 g, 109.89 mmol) in methanol (200 mL) at 0° C. The resulting mixture was then refluxed for 12 h. The reaction mixture was allowed to cool to room temperature. The yellow solid precipitated was filtered and dried to afford the title compound (22 g, yield: 100%) as a solid. 1H-NMR (CDCl3, 300 MHz): δ 8.85 (d, 1H), 7.99 (dd, 1H), 6.83 (d, 1H), 6.40 (s, 2H), 3.90 (s, 3H).

Workup

temperatureThe resulting mixture was then refluxed for 12 h
customThe yellow solid precipitated
filtrationwas filtered
customdried

Sources & evidence

ORD record: ord-79ed0dcb95ec418b81cc09537c4377b9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434697B2

Linked notes

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