Hydrazine hydrate (1:1) → HCID 178514429, compound

HRID 1255476Notes

Reaction equation

HRID 1255476 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH2:7][CH2:6]1)=O.O.[NH2:23][NH2:24]>CO>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[O:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([NH:23][NH2:24])=[O:2])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501254HCID 178501254, compound

Product 1

HCID 178514429HCID 178514429, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of trans-4-(naphthalen-2-yloxy)-cyclohexanecarboxylic acid methyl ester (0.130 g, 0.457 mmol) and hydrazine hydrate (0.02 ml, 0.45 mmol) in methanol (0.5 ml) was heated at 80° C. for 16 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 (0.112 g, 86%) as yellow solid, which was used in the next step without further purification. MS m/e: 285 (M+H+)

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-2370f2e300614791bc6cf95134b2921b
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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