Water → 2-Amino-5-chloro-3-nitrobenzoic acid

HRID 913934Notes

Reaction equation

[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:14]N1C(=O)CCC1=O.O>C(O)(=O)C>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-amino-3-nitrobenzoic acid (1 g, 5.5 mmol) in acetic acid (5 mL) at room temperature was added N-chlorosuccinimide (0.953 g, 7.14 mmol). The reaction was sealed and heated via microwave for 2 h at 80° C. The resulting mixture was poured into water (ca. 20 mL), cooled to 0° C., and the product collected by filtration. 1H-NMR (2:1 CDCl3/CD3OD, 500 MHz) δ 8.24 (d, J=2.7 Hz, 1H), 8.14 (d, J=2.8 Hz, 1H); 13C NMR (126 MHz, 2:1 CDCl3/CD3OD) δ ppm 167.8, 145.7, 139.6, 132.8, 130.9, 118.5, 116.1. Mass spec.: 215.18 (M−H)−.

Workup

customThe reaction was sealed
temperaturecooled to 0° C.
filtrationthe product collected by filtration

Sources & evidence

ORD record: ord-aab035c609d44370b34df542e5304dbd
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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