3-(4-Fluorobenzoyl)propionic acid → 3-(3,4-Dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin

HRID 973287Notes

Reaction equation

HRID 973287 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10](O)=O)=O)=[CH:4][CH:3]=1.N(CC(O)C)N.[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>>[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]2[CH2:8][CH2:9][CH:10]=[N:37][N:36]2[CH2:38][CH:39]([OH:44])[CH2:40][CH2:41][CH2:42][CH3:43])=[CH:4][CH:3]=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])[CH2:40][CH2:41][CH2:42][CH3:43])[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

7

Reactant 5

HCID 1013593-(4-Fluorobenzoyl)propionic acidHCID 2361671-Hydrazinylpropan-2-olHCID 2897634-(3,4-Dichlorophenyl)-4-oxobutyric acidHCID 41131272-HydroxybutylhydrazineHCID 203843051-Hydrazino-2-hexanol

Product 2

HCID 227511563-(3,4-Dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazinHCID 227511663-(p-Fluorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin

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-625a0ff4564d4b078f25fdb0c7d39d41
Source dataset
uspto-grants-1977_10
Patent number
US04055644

Reaction notes

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