HCID 58119712, compound → HCID 58119738, compound

HRID 2368638Notes

Reaction equation

HRID 2368638 reaction equation
[CH:1]1([CH:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[NH:9][C:8](=[O:19])[CH:7]2[C:20]#[N:21])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(#N)C.O.ClCCl>[CH:1]1([C:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:17])([CH3:18])[CH2:11][C:10]=3[NH:9][C:8](=[O:19])[C:7]=2[C:20]#[N:21])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 58119712HCID 58119712, compound

Product 1

HCID 58119738HCID 58119738, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

11.0 g 4-Cyclopentyl-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carbonitrile are suspended in 160 ml acetonitrile, heated to 60° C. and mixed dropwise with a solution of 85 g ammonium cer-(IV)-nitrate in 80 ml water. After heating for 1 h the mixture is diluted with 1200 ml dichloromethane and vigorously stirred. The aqueous bottom phase is discarded and the organic phase is washed successively with saturated sodium bicarbonate and brine. After drying with magnesium sulphate the solvents are evaporated in vacuo and the residue is triturated with diethylether. The solid is isolated by filtration, washed with diethylether and dried in vacuo.

Workup

  1. temperatureAfter heating for 1 h the mixture
  2. washthe organic phase is washed successively with saturated sodium bicarbonate and brine
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customare evaporated in vacuo
  5. customthe residue is triturated with diethylether
  6. customThe solid is isolated by filtration
  7. washwashed with diethylether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b72414aeb65f40939efaafc5ba9d2a77
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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