Acetamide → 1-Amino-5-bromoisoquinoline

HRID 2356364Notes

Reaction equation

HRID 2356364 reaction equation
[C:1]([NH2:4])(=O)[CH3:2].[Br:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1C=C[N:10]=[C:11]2Cl.C([O-])([O-])=O.[K+].[K+]>O>[Br:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:2]=[CH:1][N:4]=[C:11]2[NH2:10]

Participants

5

Reactant 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 211924975-Bromo-1-chloroisoquinoline

Product 1

HCID 337785661-Amino-5-bromoisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetamide (4.9 g, 82 mmol), 5-bromo-1-chloroisoquinoline (1.00 g, 4.1 mmol) and K2CO3 (2.8 g, 21 mmol) were combined in a sealed tube and the mixture heated at 200 C for 1.5 h. The mixture was allowed to cool to rt and the solid residue suspended in 400 mL water. The brown solid was collected as the title compound (750 mg). MS (ESI pos. ion) m/z: 223 (MH+). Calc'd exact mass for C9H7BrN2: 223.

Workup

  1. temperaturethe mixture heated at 200 C for 1.5 h
  2. customThe brown solid was collected as the title compound (750 mg)

Sources & evidence

ORD record
ord-46117b5c702e4cc5b6b1057eb8388c22
Source dataset
uspto-grants-2010_07
Patent number
US07759344B2

Reaction notes

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