Hydroxylamine → 3-Bromo-N-hydroxy-benzamidine

HRID 383764Notes

Reaction equation

HRID 383764 reaction equation
[NH2:1][OH:2].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+]>CCO>[Br:3][C:4]1[CH:5]=[C:6]([C:7](=[N:1][OH:2])[NH2:8])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 11430Potassium CarbonateHCID 233813-Bromobenzonitrile

Product 1

HCID 34578953-Bromo-N-hydroxy-benzamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Hydroxylamine (1.00 mL of a 50% aqueous solution, 16.3 mmol) was added to a solution of 3-bromobenzonitrile (750 mg, 4.12 mmol) and potassium carbonate (1.00 mg, 7.24 μmol) in EtOH (3.00 mL). The resulting mixture was heated to 120° C. in a sealed microwave vial for 40 min. After cooling to rt, the reaction mixture was concentrated in vacuo to afford the title compound i-3a. m/z (ES) 215 (MH)+.

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-86c4cd3d8d15446885678b8cdd4016b7
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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