HCID 21437938, compound → HCID 21437955, compound

HRID 2397407Notes

Reaction equation

HRID 2397407 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[C:4]([C:21]#[N:22])[CH:3]=1.[H][H]>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([OH:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:13]=2)=[C:4]([C:21]#[N:22])[CH:3]=1

Participants

5

Reactant 2

HCID 21437938HCID 21437938, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21437955HCID 21437955, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9.90 gm (0.0316 mol) of 4-(4'-chloro-2'-cyano-4-biphenylyl)-4-hydroxy-crotonic acid in 500 ml of dry ethyl acetate were hydrogenated in the presence of 2.50 gm of Raney nickel, at a hydrogen pressure of 5 atmospheres and at room temperature until the end of hydrogen absorption. After filtering, the filtrate was washed twice with 100 ml of 1% hydrochloric acid each and then with water, dried over sodium sulfate and evaporated in vacuo. The oily, yellowish residue was dissolved in ethyl acetate and converted into the cyclohexylamine salt by addition of the equimolar quantity of cyclohexylamine. Yield: 6.15 gm; m.p. 168°-169° C. (from acetone/ethyl acetate 1:1).

Workup

  1. filtrationAfter filtering
  2. washthe filtrate was washed twice with 100 ml of 1% hydrochloric acid each and then with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe oily, yellowish residue was dissolved in ethyl acetate
  6. additionconverted into the cyclohexylamine salt by addition of the equimolar quantity of cyclohexylamine

Sources & evidence

ORD record
ord-3766b366182848ddac4f134fb5a414c0
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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