3-Chloroaniline → HCID 9999066, compound

HRID 1787494Notes

Reaction equation

HRID 1787494 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)N>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:28]1[CH:27]=[CH:25][CH:24]=[C:23]([Cl:22])[CH:29]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 9999066HCID 9999066, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (100 mg, 0.34 mmol) (Dal Piaz, V et al., J. Med. Chem. 1997, 40, 1417) in ethanol (2 mL), 3-chloroaniline (132 mg, 1.04 mmol) was added portionwise. The resulting mixture was stirred at room temperature for 30 min and the final product was collected by filtration and washed with ethanol and diethylether to yield the title compound (65% yield).

Workup

  1. filtrationthe final product was collected by filtration
  2. washwashed with ethanol and diethylether

Sources & evidence

ORD record
ord-442a8a8e08764f4fb92039d87576846b
Source dataset
uspto-grants-2009_03
Patent number
US07511038B2

Reaction notes

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