Hydrazine hydrate (1:1) → HCID 178491492, compound

HRID 1255471Notes

Reaction equation

HRID 1255471 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:7][CH2:6]1)=O.O.[NH2:21][NH2:22]>>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([NH:21][NH2:22])=[O:2])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178491493HCID 178491493, compound

Product 1

HCID 178491492HCID 178491492, compoundYield 93.3%

Conditions

Temperature
120 °C

Procedure

A mixture of trans-4-(3-methoxy-phenoxy)-cyclohexanecarboxylic acid methyl ester (0.20 g, 0.75 mmol) and hydrazine hydrate (0.035 ml, 0.73 mmol) was heated at 120° C. for 22 h. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (50 ml) and 1 M aqueous sodium hydroxide solution (50 ml). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (0.18 g, 92%) as white solid, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between ethyl acetate (50 ml) and 1 M aqueous sodium hydroxide solution (50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c87e12f8367c4c5aa390116a67295bba
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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