Ammonia → 3-(6-Amino-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide

HRID 1097319Notes

Reaction equation

Cl[CH:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([NH:13][CH3:14])=[O:12])=[CH:3]1.[NH3:18]>CCO>[NH2:18][CH:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([NH:13][CH3:14])=[O:12])=[CH:3]1

Participants

Conditions

Temperature: 160 °C

Procedure

3-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide (1 eq, 2.46 mmol, 610 mg) is dissolved in a solution of NH3 (7N, 20 ml) in EtOH and heated at 160° C. in a sealed tube for 48 h. The solvent is then removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 8:2:0.5 DCM/MeOH/NH3 to give 3-(6-Amino-1,6-dihydro-pyridazin -4-yl)-N-methyl-benzamide as a brown solid; [M+H]+=229

Workup

customThe solvent is then removed in vacuo
customThe reaction mixture is purified by flash column chromatography
washeluting with 8:2:0.5 DCM/MeOH/NH3

Sources & evidence

ORD record: ord-2051635063f043a298c5df2b80d2db69
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143253B2

Reaction notes

Loading…