Hydroxylamine → 16348-49-5

HRID 557998Notes

Reaction equation

HRID 557998 reaction equation
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH2:10][OH:11]>CCO>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1](=[N:10][OH:11])[NH2:9]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 729132-Aminobenzonitrile

Product 1

HCID 363347816348-49-5Yield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anthranilonitrile (1 g, 8.5 mmol) and hydroxylamine (50% in water, 0.57 cm3, 9.3 mmol, 1.1 eq) in EtOH (42.5 cm3) were stirred under reflux for 24 hours, after which the volatiles were removed under reduced pressure and residue was partitioned between water (5 cm3) and CH2Cl2 (100 cm3). The organic phase was evaporated to dryness in the rotary evaporator followed by high vacuum line to give the product 2-amino-N′-hydroxybenzimidamide (1.16 g, 90.3%) as a solid, mp 85-86° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customafter which the volatiles were removed under reduced pressure and residue
  3. customwas partitioned between water (5 cm3) and CH2Cl2 (100 cm3)
  4. customThe organic phase was evaporated to dryness in the rotary evaporator

Sources & evidence

ORD record
ord-717c651b959e40fdaa39fb1be2c7692b
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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