Hexane → HCID 178468081, compound

HRID 2118986Notes

Reaction equation

HRID 2118986 reaction equation
[C:1]1([N:7]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[C:8]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC>[Pd].CN(C)C=O>[NH2:12][C:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[C:10]([C:14](=[O:13])[CH3:15])[C:8]([N:7]([CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

5

Reactant 2

HCID 8058HexaneHCID 13982559N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide

Product 1

HCID 178468081HCID 178468081, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 35 grams (0.1 mole) of N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide and 3.8 grams of 10% palladium on carbon in 200 milliliters of dimethylformamide is hydrogenated at 50 psi and 50°-60° C. overnight. The mixture is cooled, filtered, and the filtrate evaporated in vacuo. The residue obtained is then treated with hexane and the resulting crystals triturated with ether to give 2-(aminophenylmethylene)-N-(2-dimethylaminoethyl)-N-phenyl-3-oxobutanamide; M.P. 81°-83° C.

Workup

  1. customis hydrogenated at 50 psi and 50°-60° C. overnight
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customThe residue obtained
  6. customthe resulting crystals triturated with ether

Sources & evidence

ORD record
ord-ea58c8cd8b674510961573e06adcc6e2
Source dataset
uspto-grants-1987_07
Patent number
US04681898

Reaction notes

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