2-Amino-5-nitropyridine → 5-Acetyl-2-ethyl-4-[(5-nitropyridin-2-yl)amino]-6-phenylpyridazin-3(2H)-one

HRID 1725524

Reaction equation

HRID 1725524 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].N[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 778882-Amino-5-nitropyridineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 684856525-Acetyl-2-ethyl-4-[(5-nitropyridin-2-yl)amino]-6-phenylpyridazin-3(2H)-oneYield 34.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 80 mg (0.278 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in 4 ml of ethanol, 77 mg (0.556 mmol) of 2-amino-5-nitropyridine was added. The resulting mixture was irradiated in microwave oven for seven hours at 120° C. The final product was collected by filtration and washed with diethylether to yield the title compound (36 mg, 34.3% yield).

Workup

  1. customThe resulting mixture was irradiated in microwave oven for seven hours at 120° C
  2. filtrationThe final product was collected by filtration
  3. washwashed with diethylether

Sources & evidence

ORD record
ord-67dbdc8ca383432ba7cf92a6e4da058c
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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