Acetic Acid → HCID 19967810, compound

HRID 867898Notes

Reaction equation

HRID 867898 reaction equation
C(O)(=O)C.[C:5]([N:8]1[C:12]2=[CH:13][C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:15][N:11]2[C:10]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([N+:28]([O-])=O)[C:21]=2[CH3:31])=[N:9]1)(=[O:7])[CH3:6].[H][H]>[Ni].C1COCC1>[C:5]([N:8]1[C:12]2=[CH:13][C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:15][N:11]2[C:10]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([NH2:28])[C:21]=2[CH3:31])=[N:9]1)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21288865HCID 21288865, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19967810HCID 19967810, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.5 ml) was added to Raney nickel (8 spoon-spatulas full) and after washing with THF the catalyst was added to the product of part (a) (16.6 g, 44.9 mmole) in THF (160 ml). The resulting mixture was shaken in an atmosphere of hydrogen at atmospheric pressure for 4 hours and then filtered, the catalyst washed with THF and the filtrate evaporated to give a solid (14.1 g). This material was chromatographed on a dry deactivated silica gel column eluting with 1% ethyl acetate in methylene chloride to give the partially hydrated product, m.p. 206°-207° C., 12.7 g (83%).

Workup

  1. washafter washing with THF the catalyst
  2. filtrationfiltered
  3. washthe catalyst washed with THF
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-71abcde067a74487a2608ca7793b6a00
Source dataset
uspto-grants-1988_10
Patent number
US04777121

Reaction notes

Loading…