Hydrazine hydrate (1:1) → HCID 19030721, compound

HRID 1708309Notes

Reaction equation

HRID 1708309 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[C:31]([O:33][CH2:34][CH3:35])[CH:30]=[CH:29][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH:16]([C:24]([O:26]CC)=O)[C:14]2=[O:15])[CH2:9][CH2:8]1)=[O:6].O.[NH2:37][NH2:38]>C(O)C>[CH3:1][O:2][C:3]1[CH:32]=[C:31]([O:33][CH2:34][CH3:35])[CH:30]=[CH:29][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH:16]([C:24]([NH:37][NH2:38])=[O:26])[C:14]2=[O:15])[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030985HCID 19030985, compound

Product 1

HCID 19030721HCID 19030721, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-[1-(2-methoxy-4-ethoxybenzoyl)-4-piperidinyl]-3-ethoxycarbonyl-3,4-dihydrocarbostyril (1.1 g) are added hydrazine monohydrate (1.1 g) and ethanol (15 ml) and the mixture is refluxed with heating for 7 hours. The reaction mixture is concentrated and the residue is purified by silica gel column chromatography (solvent: dichloromethane→dichloromethane:methanol=20:1) to give 1-[1-(2-methoxy-4-ethoxybenzoyl)4-piperidinyl]-3-hydrazinocarbonyl-3,4-dihydrocarbostyril (0.9 g) as white amorphous form.

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 7 hours
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is purified by silica gel column chromatography (solvent: dichloromethane→dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-28a9092ed18d4e358c6fcd6edc3effc9
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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