Nitric Acid → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

HRID 1768451Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[Br:14].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5]([Br:14])=[CH:6][CH:7]=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[C:9]=1[N+:16]([O-:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-acetylamino-2-bromo-benzoic acid methyl ester (ii, 5.44 g, 20.0 mmol) in H2SO4 (50 mL) at 0° C. was added HNO3 (50 mL). The reaction mixture was stirred at 0° C. for 20 min and poured into ice water (200 mL). The mixture was then extracted with EtOAc (3×200 mL). The combined extracts were washed with saturated aqueous NaHCO3 (3×200 mL), H2O (3×200 mL), brine (1×200 mL), and dried with Na2SO4. Flash column chromatography gave the desired product iii as a yellow solid (3.60 g, 57%). 1H NMR (acetone-d6): δ 9.47 (br s, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.89 (d, J=9.0, 1H), 3.84 (s, 3H), 2.10 (s, 3H). Anal. Calcd for C10H9BrN2O5: C, 37.88; H, 2.86; N, 8.83. Found: C, 38.02; H, 2.74; N, 8.74.

Workup

extractionThe mixture was then extracted with EtOAc (3×200 mL)
washThe combined extracts were washed with saturated aqueous NaHCO3 (3×200 mL), H2O (3×200 mL), brine (1×200 mL)
dry with materialdried with Na2SO4

Sources & evidence

ORD record: ord-ceefa06a3c2742c789e5c5644c22755a
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235662B2

Reaction notes

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