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

HRID 1417186Notes

Reaction equation

HRID 1417186 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 hydrogen carbonate. 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 silica gel column chromatography (hexane/ethyl acetate=1/1), followed by crystallization from hexane to afford 4.41 g of the title 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 silica gel column chromatography (hexane/ethyl acetate=1/1)
  4. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-4a6c9e1932b6473386e78a32bd79f87d
Source dataset
uspto-grants-1999_03
Patent number
US05876756

Reaction notes

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