3-(4-Fluorobenzoyl)propionic acid → 3-(3,4-Dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin
Reaction equation
F[C:2]1[CH:14]=C[C:5]([C:6]([CH2:8][CH2:9][C:10](O)=O)=[O:7])=[CH:4][CH:3]=1.[NH:15](CC(O)C)[NH2:16].[Cl:21][C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:25]([CH2:27][CH2:28][C:29](O)=O)=O.[NH:36]([CH2:38][CH:39]([OH:44])[CH2:40][CH2:41][CH2:42][CH3:43])[NH2:37].N(CC(O)CC)N>>[OH:7][CH:6]([CH2:8][CH2:9][CH2:10][CH3:22])[CH2:5][C:4]1[CH2:3][CH2:2][CH:14]=[N:16][N:15]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:25]2[CH2:27][CH2:28][CH:29]=[N:37][N:36]2[CH2:38][CH:39]([OH:44])[CH3:40])[CH:32]=[CH:33][C:34]=1[Cl:35].[Cl:21][C:22]1[CH:23]=[C:24]([CH:25]2[CH2:27][CH2:28][CH:29]=[N:37][N:36]2[CH2:38][CH:39]([OH:44])[CH2:40][CH2:41][CH2:42][CH3:43])[CH:32]=[CH:33][C:34]=1[Cl:35]Participants
8
Reactant 5
Product 3
Procedure
When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4 dichlorobenzoyl)-propionic acid and 1-hydrazino -2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl-4,5-dihydropyridazin (2H)-3-one(m.p. 75°-77°C) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 108.5° - 100°C) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one(m.p. 80°-81°C) respectively.
Sources & evidence
- ORD record
- ord-da273afb645c4525ab78720ba32d093e
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931176
Reaction notes
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