Hydrazine hydrate (1:1) → HCID 21193747, compound

HRID 582132Notes

Reaction equation

HRID 582132 reaction equation
[C:1]([CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:12]=1)[C:5](OCC)=[O:6])(=O)[CH3:2].O.[NH2:26][NH2:27]>C(O)C>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=2[O:17][CH3:18])[CH2:10][C:4]2[C:5](=[O:6])[N:26]=[N:27][C:1]=2[CH3:2])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21193739HCID 21193739, compound

Product 1

HCID 21193747HCID 21193747, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ethyl 2-acetyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-propanoate (585 mg, 1.74 mmol) in absolute ethanol (10 ml) at 0° C. was added hydrazine monohydrate (87 mg, 1.74 mmol) in one portion. The resulting solution was stirred at 0° C. for 45 minutes and then refluxed at 80° C. for 3 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo and purified by flash chromatography (SiO2 ; methylene chloride/ethanol/ammonia (4:1:0.1)) to afford the title compound as a white solid (343 mg). m.p. 186-187° C.

Workup

  1. temperaturerefluxed at 80° C. for 3 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. custompurified by flash chromatography (SiO2 ; methylene chloride/ethanol/ammonia (4:1:0.1))

Sources & evidence

ORD record
ord-8c937698437743419181139746b282a2
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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