Ammonia → HCID 14698593, compound

HRID 846209Notes

Reaction equation

HRID 846209 reaction equation
[C:1]([C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2].[H][H].N.Cl>[Ni].C(O)C>[NH2:2][CH2:1][C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:8][CH:7]=1)([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14698596HCID 14698596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14698593HCID 14698593, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

5 g. N-[4-(1-Cyano-1-methylethyl)-phenyl]-4-methoxybenzamide (Example 27) are hydrogenated at 90° C. and 120 bar hydrogen pressure in 40 ml. ethanol in the presence of 40 ml. liquid ammonia and 2 g. Raney nickel. The reaction mixture is filtered and the filtrate evaporated to dryness in a vacuum. After column chromatographic purification (400 ml. silica gel 60; dichloromethane/methanolic ammonia 30:1 v/v), there are obtained 2.6 g. of colourless crystals which are heated in 100 ml. 1M hydrochloric acid. After cooling, there are obtained 2.3 g. (40% of theory) of the title compound as hydrochloride in the form of colourless leaflets; m.p. 273°-276° C.

Workup

  1. customare hydrogenated at 90° C.
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated to dryness in a vacuum
  4. customAfter column chromatographic purification (400 ml. silica gel 60; dichloromethane/methanolic ammonia 30:1 v/v), there
  5. customare obtained 2.6 g
  6. temperatureof colourless crystals which are heated in 100 ml
  7. temperatureAfter cooling
  8. customthere are obtained 2.3 g

Sources & evidence

ORD record
ord-0cc1526a98bf47ee9fa57d8ca8ef0b4e
Source dataset
uspto-grants-1992_08
Patent number
US05135949

Reaction notes

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