Isatoic Anhydride → HCID 103821981, compound

HRID 523207Notes

Reaction equation

HRID 523207 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[O:3]C1=O.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([Br:13])[C:15]=1[CH3:21])=[O:3]

Participants

3

Reactant 2

HCID 8359Isatoic AnhydrideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 103821981HCID 103821981, compoundYield 24.5%

Procedure

A suspension of 1H-benzo[d][1,3]oxazine-2,4-dione (5.00 g, 30.7 mmol) and 3-bromo-2-methylaniline (5.70 g, 30.7 mmol) in xylenes (50 mL) was heated at reflux for 8 h. The solvent was removed by distillation and the residue was purified by column chromatography on silica gel (120 g), eluting with EtOAc-hexanes (gradient from 0-50%), to give 2-amino-N-(3-bromo-2-methylphenyl)benzamide as an off-white solid (2.30 g, 24% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. customThe solvent was removed by distillation
  4. customthe residue was purified by column chromatography on silica gel (120 g)
  5. washeluting with EtOAc-hexanes (gradient from 0-50%)

Sources & evidence

ORD record
ord-2e9eee3b4d4844dd9ac9638cb79dec08
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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