Benzonitrile, 2-amino-4-chloro- → 2-amino-4-chloro-N-hydroxy-benzamide

HRID 2111958Notes

Reaction equation

HRID 2111958 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1C#N.Cl.[NH2:12][OH:13].[C:14](=[O:17])(O)[O-].[Na+]>C(O)C.O>[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:14]([NH:12][OH:13])=[O:17]

Participants

6

Reactant 3

HCID 170059Benzonitrile, 2-amino-4-chloro-HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 117081892-amino-4-chloro-N-hydroxy-benzamideYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Amino-4-chloro-benzonitrile (5.3 g, 35 mmol) was dissolved in ethanol (180 ml) aided by heating. An aqueous solution of hydroxylamine hydrochloride (4.9 g, 70 mmol) and sodium bicarbonate (11.1 g, 105 mmol) was added and the mixture was refluxed for 8 hours. The solvent was then reduced and the product suspended in water (100 ml) and filtered off to yield 5.6 g (86%) of a white powder (m.p. 131-133° C.).

Workup

  1. temperatureby heating
  2. temperaturethe mixture was refluxed for 8 hours
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-302d06d2abf944acaf1dccb1226c25ea
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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