Chloroacetyl chloride → N'-(chloroacetyl)-3-(methyloxy)-4-nitrobenzohydrazide

HRID 419335Notes

Reaction equation

HRID 419335 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([NH:8][NH2:9])=[O:7].[Cl:16][CH2:17][C:18](Cl)=[O:19]>CCOC(C)=O>[Cl:16][CH2:17][C:18]([NH:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 218838753-Methoxy-4-nitrobenzohydrazide

Product 1

HCID 59452892N'-(chloroacetyl)-3-(methyloxy)-4-nitrobenzohydrazideYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3-(methyloxy)-4-nitrobenzohydrazide (3.65 g, 17.3 mmol) in EtOAc (150 mL) was added chloroacetyl chloride (1.50 mL, 18.8 mmol). The reaction was stirred open to air overnight. The solid was filtered and washed with diethyl ether to provide the title compound (3.17 g, 11.0 mmol, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.98 (s, 3H), 4.21 (s, 2H), 7.56 (dd, J=8.2, 1.6 Hz, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H), 10.48-10.54 (m, 1H), 10.82 (d, J=1.5 Hz, 1H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-745fc27ce7ca455fa04f08fd189a966d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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