HCID 14403640, compound → HCID 14403634, compound

HRID 1194149Notes

Reaction equation

HRID 1194149 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:10]([C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C:8]2[N:26]=[CH:27][N:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[C:32]([CH3:39])[CH:31]=3)[C:7]=2[CH2:6]1)=[O:4]>O1CCCC1CO.[Ni]>[CH3:1][O:2][C:3]([CH:5]1[N:10]([C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][C:8]2[N:26]=[CH:27][N:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([CH3:39])[CH:31]=3)[C:7]=2[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 14403640HCID 14403640, compound

Product 1

HCID 14403634HCID 14403634, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A solution of 31.2 g methyl-1-(4-nitro-3-methylphenyl)methyl-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate in tetrahydrofuran-methanol (2:1, 600 mL) is treated with 8.0 g Raney Nickel and placed under an atmosphere of hydrogen at 50 psi for 26 hr. The catalyst is removed by filtration and filtrate is evaporated to give a crisp foam. NMR (CDCl3) 6.77 (s+d,2H,2,6-Ar); 6.60 (d,1H,5-Ar). mp 182°-188° C.

Workup

  1. customThe catalyst is removed by filtration and filtrate
  2. customis evaporated
  3. customto give a crisp foam

Sources & evidence

ORD record
ord-8cca16b3a8c741c0bcf91183eae99242
Source dataset
uspto-grants-1989_03
Patent number
US04812462

Reaction notes

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