Hydrazine hydrate (1:1) → HCID 178514442, compound

HRID 1255479Notes

Reaction equation

HRID 1255479 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)[CH2:7][CH2:6]1)=O.O.[NH2:20][NH2:21]>C(O)CCC>[Cl:18][C:16]1[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)[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501282HCID 178501282, compound

Product 1

HCID 178514442HCID 178514442, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trans-4-(5-chloro-pyridin-3-yloxy)-cyclohexanecarboxylic acid methyl ester (0.19 g, 0.70 mmol) and hydrazine hydrate (0.14 ml, 2.8 mmol) in n-butanol (0.5 ml) was heated at 120° C. for 18 h. After cooling to room temperature the reaction mixture was triturated in toluene (100 ml). The product was collected by filtration and dried in vacuo to give the crude title compound (0.15 g, 79%) as white solid, which was used in the next step without further purification. MS m/e: 270 (M+H+)

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas triturated in toluene (100 ml)
  3. filtrationThe product was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2f661d98dcfb4db1a2a472b01510fb55
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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