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

HRID 464946Notes

Reaction equation

HRID 464946 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 962Water2×HCID 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

15.3 g of p-nitrophenylhydrazine and 10.1 g of triethylamine were dissolved in 100 ml of acetonitrile, and 7.9 g of acetyl chloride was added dropwise over 15 minutes with cooling with water. After conclusion of the addition, the mixture was stirred at 25° C. for 1 hour and thereafter 100 ml of water as added thereto. The precipitated crystals were filtered off, and washed with acetonitrile to obtain 16.6 g of 1-acetyl-2-(4-nitrophenyl)hydrazine. Yield: 16.6 g. Melting point: 209°-214° C.

Workup

  1. additionAfter conclusion of the addition
  2. filtrationThe precipitated crystals were filtered off
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-b65e700ecfd3487882665c1c0ba8bfa2
Source dataset
uspto-grants-1985_10
Patent number
US04550070

Reaction notes

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