3-Aminobenzamide → 3-Nitrosobenzamide

HRID 374900

Reaction equation

HRID 374900 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].ClC1C=C(C=CC=1)C(OO)=[O:16]>C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])=[O:16]

Participants

4

Reactant 2

HCID 16453-AminobenzamideHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 16793-NitrosobenzamideYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-aminobenzamide (Aldrich Chemical Co.) (0.476 g, 3.50 mmol) in ethyl acetate (50 ml) at ambient temperature was added 1.208 g of 3-chloroperoxybenzoic acid (commercial grade, 50-60% purity, Aldrich), whereupon the solution turned green. After 10 minutes the mixture was extracted with 0.14 M aqueous sodium bicarbonate (58 ml), washed with three successive 40-ml portions of water, dried over sodium sulfate, then reduced in volume to 20 mL by rotary evaporation and placed in the freezer (-20° C.), whereupon the product slowly deposited as a light yellow solid during a period of 72 hours (0.180 g, 34% yield).

Workup

  1. extractionAfter 10 minutes the mixture was extracted with 0.14 M aqueous sodium bicarbonate (58 ml)
  2. washwashed with three successive 40-ml portions of water
  3. dry with materialdried over sodium sulfate
  4. customreduced in volume to 20 mL by rotary evaporation
  5. customplaced in the freezer (-20° C.), whereupon the product

Sources & evidence

ORD record
ord-3647d8b670e64a9eacf4159f3fbf846e
Source dataset
uspto-grants-1996_01
Patent number
US05482975

Linked notes

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