HCID 21437942, compound → HCID 19036864, compound

HRID 2397376Notes

Reaction equation

HRID 2397376 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1.[H][H]>C(O)(=O)C.Cl(O)(=O)(=O)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 21437942HCID 21437942, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19036864HCID 19036864, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 24247Perchloric AcidSolvent

Procedure

13.7 gm (0.05 mol) of 4-(2'-fluoro-4-biphenylyl)-4-oxo-crotonic acid in 100 ml of glacial acetic acid and 2 ml of perchloric acid were hydrogenated in the presence of 4 gm of 5% palladium/barium sulfate at room temperature and at atmospheric pressure; the reaction was finished after absorption of 3 mols of hydrogen. After filtering, the mixture was evaporated in vacuo, the residue distributed between water and ethyl acetate and the ethyl acetate phase was evaporated. The residue was crystallized from cyclohexane. Yield: 11.1 gm (61.4% of theory); m.p. 65°-66° C. Melting point of the cyclohexylamine salt: 130°-132° C. Melting point of the sodium salt: 139°-141° C. Melting point of the isobutylamine salt: 92°-93° C. (from ethyl acetate).

Workup

  1. filtrationAfter filtering
  2. customthe mixture was evaporated in vacuo
  3. customthe ethyl acetate phase was evaporated
  4. customThe residue was crystallized from cyclohexane
  5. custom130°-132° C
  6. custom139°-141° C
  7. custom92°-93° C. (from ethyl acetate)

Sources & evidence

ORD record
ord-8c6c014c202a4583a49c37607d0c8169
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

Loading…