HCID 22922500, compound → HCID 22922550, compound

HRID 2258544Notes

Reaction equation

HRID 2258544 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:10]=3[N:9]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=3[O:29][CH3:30])[C:8]2=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[Ni]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:9]2[C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][C:11]=3[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]2=[O:31])=[C:21]([O:29][CH3:30])[CH:22]=1

Participants

4

Reactant 1

HCID 22922500HCID 22922500, compound

Product 1

HCID 22922550HCID 22922550, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.5 g of the compound obtained in Example 5 in 350 ml of absolute EtOH, in the presence of Raney nickel, is hydrogenated for 20 hours at RT and at a pressure of 60 bar. The reaction mixture is filtered on Celite and the filtrate is evaporated under vacuum. The residue is chromatographed on silica, eluting with a DCM/EtOAc mixture (90/10; v/v). 2.7 g of the expected product are obtained after crystallization from an iso ether/EtOAc mixture, mp=191° C.

Workup

  1. filtrationThe reaction mixture is filtered on Celite
  2. customthe filtrate is evaporated under vacuum
  3. customThe residue is chromatographed on silica
  4. washeluting with a DCM/EtOAc mixture (90/10; v/v)

Sources & evidence

ORD record
ord-d4459186c0644fc696fe73c2cf569c98
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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