Water → 4-(Amino-hydroxyimino)methylbenzoic acid methyl ester

HRID 376536

Reaction equation

HRID 376536 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.Cl.[NH2:14][OH:15].C(=O)([O-])O.[Na+].O>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[N:11][O:15][NH2:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70791Methyl 4-cyanobenzoateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 543937604-(Amino-hydroxyimino)methylbenzoic acid methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 200 ml of methanol were dissolved 16.5 g of 4-cyanobenzoic acid methyl ester and 7.2 g of hydroxylamine hydrochloride. To the solution was added 8.82 g of sodium hydrogencarbonate at room temperature. The mixture was heated for 3 hours under reflux. The reaction mixture was cooled, to which was added 400 ml of water. Resulting crystalline precipitate was collected by filtration, which was washed with water and ether, followed by drying under reduced pressure to afford 16.1 g of the titled compound as colorless needles.

Workup

  1. temperatureThe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled, to which
  4. filtrationResulting crystalline precipitate was collected by filtration, which
  5. washwas washed with water and ether
  6. customby drying under reduced pressure

Sources & evidence

ORD record
ord-6695f32bf3964c77b3ffb225e94d8322
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Linked notes

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