Ammonia → 6-(4-amino-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

HRID 1031428Notes

Reaction equation

HRID 1031428 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[NH3:19]>C(O)C>[NH2:19][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 31111876-(4-amino-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g of 6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one, 50 ml of 25% aqueous NH3 solution and 50 ml of ethanol is heated at 100° for 16 hours. The mixture is poured into ice water and extracted with methylene dichloride, the phases are separated and the organic phase is dried over sodium sulfate and evaporated to give 6-(4-amino-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one, m.p. 234°-238°.

Workup

  1. temperatureis heated at 100° for 16 hours
  2. extractionextracted with methylene dichloride
  3. customthe phases are separated
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-80a9b51fb2b5469085bb28abf00d12d2
Source dataset
uspto-grants-1990_09
Patent number
US04954499

Reaction notes

Loading…