4-Nitroanthranilic acid → Methyl 4-nitroanthranilate

HRID 1392258Notes

Reaction equation

HRID 1392258 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C1C=CC=CC=1.CO>[CH3:15][O:9][C:8](=[O:10])[C:7]1[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[NH2:13]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 596476Methyl 4-nitroanthranilateYield 86.1%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a solution of 4-nitro-anthranilic acid (2.200 g, 10.9 mmol, 1 eq) in benzene/methanol (4/1) (100 mL) was added TMSCHN2 (2M in hexanes) (12 mL, 24 mmol, 2.2 eq). The reaction was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 4-nitro-anthranilic acid methyl ester (1.841 g, 86%) as a bright yellow solid. 1H NMR (300 MHz, CDCl3); δ 8.00 (d, 1H), 7.50 (d, 1H), 7.40 (dd, 1H), 3.92 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ebd772e72f7242e7a6ded877d57bb632
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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