Hexane → Methyl 2-acetylamino-4-nitrobenzoate

HRID 350571Notes

Reaction equation

HRID 350571 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C.CCCCCC>C1C=CC=CC=1.CO>[C:1]([NH:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:17])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 70373Benzoic acid, 2-(acetylamino)-4-nitro-HCID 167693Trimethylsilyldiazomethane

Product 1

HCID 12399497Methyl 2-acetylamino-4-nitrobenzoateYield 97.1%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a stirred solution of 2-acetylamino-4-nitrobenzoic acid (1.28 g, 5.71 mmol) in benzene-MeOH (4:1, v/v, 25 mL), was added trimethylsilyldiazomethane (2.0 M solution in n-hexane, 4.28 ml, 8.56 mmol) at 0° C. The stirring was continued for 18 hours at rt. The reaction was poured into hexane, and the resulting precipitate was collected by filtration to give methyl 2-acetylamino-4-nitrobenzoate (1.32 g, 97%) as a white solid; mp no data; 1H-NMR (400 MHz, CDCl3) δ 2.30 (s, 3 H), 4.00 (s, 3 H), 7.88 (m, 1 H), 8.18 (dd, J=2.0 Hz, 8.8 Hz, 1 H), 9.60 (t, J=2.2 Hz, 1 H), 11.10 (s, 1 H); MS (ESI) m/z 238 (M+).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-02fddc18c3bf4fb58c295ddad0071c35
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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