Water → Acetic acid, 2-(4-nitrophenyl)hydrazide

HRID 648899Notes

Reaction equation

HRID 648899 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].O>C(#N)C>[C:19]([NH:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 3404344Acetic acid, 2-(4-nitrophenyl)hydrazideYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

In 100 ml of acetonitrile were dissolved 15.3 g of p-nitrophenylhydrazine and 10.1 g of triethylamine, and 7.9 g of acetyl chloride was added dropwise to the solution under ice-cooling over a period of 15 minutes. Thereafter, the mixture was stirred for 1 hour at 25° C., 100 ml of water was added therreto, and crystals thus deposited were collected by filtration and washed with acetonitrile to provide 16.6 g of 1-acetyl-2-(4-nitrophenyl)hydrazine. The melting point was 209°-214° C.

Workup

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling over a period of 15 minutes
  3. filtrationthus deposited were collected by filtration
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-15c10e3a5f594409860e99960babacdf
Source dataset
uspto-grants-1988_04
Patent number
US04737452

Reaction notes

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