3-Bromo-o-toluidine → 2-amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamide

HRID 523199Notes

Reaction equation

HRID 523199 reaction equation
[F:1][C:2]1[C:7]2[NH:8]C(=O)[O:10][C:11](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:14][C:15]1[C:16]([CH3:22])=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([Br:14])[C:16]=1[CH3:22])=[O:10]

Participants

3

Reactant 2

HCID 1235383-Bromo-o-toluidineHCID 105353938-Fluoroisatoic anhydride

Product 1

HCID 1076251882-amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamideYield 84%

Procedure

A suspension of 8-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (3.00 g, 16.6 mmol) in xylenes (50 mL) was treated with 3-bromo-2-methylaniline (3.08 g, 16.6 mmol) and heated to reflux. After 6 h the mixture was allowed to cool to room temperature overnight. The resulting suspension was diluted with hexanes and the precipitate was collected by filtration, rinsed with hexanes and air-dried to provide 2-amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamide as a white solid (4.50 g, 84% yield). 1H NMR (400 MHz, chloroform-d) δ 7.69 (d, J=7.9 Hz, 1H), 7.65 (br. s., 1H), 7.50-7.46 (m, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.19-7.11 (m, 2H), 6.73-6.64 (m, 1H), 5.69 (br. s., 2H), 2.44 (s, 3H).

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate was collected by filtration
  3. washrinsed with hexanes
  4. customair-dried

Sources & evidence

ORD record
ord-1e4f9646d4cc4d05b09951b48e61dd7f
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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