Hydroxylamine → 4-t-Butoxycarbonyl benzaldoxime

HRID 1417192Notes

Reaction equation

HRID 1417192 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].N[OH:17].C(N(CC)CC)C>CO>[C:1]([O:5][C:6]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[N:14][OH:17])=[CH:11][CH:12]=1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8471TriethylamineHCID 271408Tert-butyl 4-cyanobenzoate

Product 1

HCID 867537874-t-Butoxycarbonyl benzaldoximeYield 51.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 100 ml of methanol was dissolved 20.5 g of 4-cyanobenzoic acid t-butyl ester and 13.9 g of hydroxylamine. To the solution was added, while stirring at room temperature, 128 g of triethylamine; The resulting mixture was stirred for one hour at 85° C. then concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate, and the solution was washed with water. The organic layer was concentrated under reduced pressure to give a crude product, which was recrystallized from isopropyl ether to afford 11.45 g of the title compound as a colorless crystalline product.

Workup

  1. additionTo the solution was added
  2. stirringThe resulting mixture was stirred for one hour at 85° C.
  3. concentrationthen concentrated under reduced pressure
  4. dissolutionThe concentrate was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customto give a crude product, which
  8. customwas recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-c84682fbb4e8486a8af8cda40518156c
Source dataset
uspto-grants-1999_03
Patent number
US05876756

Reaction notes

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