Hydrazine hydrate (1:1) → HCID 178514437, compound

HRID 1516176Notes

Reaction equation

HRID 1516176 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][C:15]([F:18])=[CH:14][N:13]=2)[CH2:7][CH2:6]1)=O.O.[NH2:20][NH2:21]>C(O)CCC>[F:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@H:8]2[CH2:9][CH2:10][C@H:5]([C:3]([NH:20][NH2:21])=[O:2])[CH2:6][CH2:7]2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501277HCID 178501277, compound

Product 1

HCID 178514437HCID 178514437, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of trans-4-(5-fluoro-pyridin-2-yloxy)-cyclohexanecarboxylic acid methyl ester (0.92 g, 3.6 mmol) and hydrazine hydrate (0.80 ml, 16 mmol) in n-butanol (1 ml) was heated at 125° C. for 4 h. After cooling to room temperature the reaction mixture was partitioned between dichloromethane (75 ml) and water (75 ml). The aqueous layer was washed with dichloromethane/75 ml). The combined organic layers were washed with water (75 ml) and brine (75 ml), dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (0.55 g, 67%) as white solid, which was used in the next step without further purification. MS m/e: 254 (M+H+)

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between dichloromethane (75 ml) and water (75 ml)
  3. washThe aqueous layer was washed with dichloromethane/75 ml)
  4. washThe combined organic layers were washed with water (75 ml) and brine (75 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-199a39177e01474f9edf957afde7aa87
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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