Tert-butyl 4-cyanobenzoate → 4-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester

HRID 1585087Notes

Reaction equation

HRID 1585087 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][OH:18].C(=O)([O-])O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[N:14][O:18][NH2:17])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 271408Tert-butyl 4-cyanobenzoateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 544161174-(Amino-hydroxyimino)methylbenzoic acid t-butyl esterYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

In a mixture of 21.2 ml of t-butanol and 2.1 ml of water were dissolved 4.3 g of 4-cyanobenzoic t-butyl ester, 1.84 g of hydroxylamine hydrochloride and 2.31 g of sodium hydrogencarbonate. The solution was stirred for 2 hours at 80° C. To the reaction mixture was added water, and the mixture was subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate=1/1), followed by crystallization from hexane to afford 4.41 g of the titled compound as colorless needles.

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate=1/1)
  4. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-c7f284ec120c40a2a8c470d5ad8b6cde
Source dataset
uspto-grants-1999_08
Patent number
US05935963

Reaction notes

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