5-Bromoisatoic Anhydride → 2-Amino-5-bromo-N-methylbenzamide

HRID 2279718Notes

Reaction equation

HRID 2279718 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7](OC(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH3:14][NH2:15].C1COCC1>C1COCC1>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=1[C:7]([NH:15][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 2885615-Bromoisatoic AnhydrideHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 509995112-Amino-5-bromo-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromoisatoic anhydride (4.84 g, 20.0 mmol) in THF (20 mL) was added 2M MeNH2/THF (15 mL, 30 mmol). The resulting mixture was stirred at rt overnight. The solvent was evaporated under reduced pressure and the crude material was used in next step without further purification. MS (ESI): m/z=229.03/231.06 [M+H]+. HPLC: tR=3.14 min (ZQ3: polar—5 min).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude material was used in next step without further purification
  3. customHPLC: tR=3.14 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-da1eb6f5aab544f0b1be4cc1c86a0142
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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