HCID 13423628, compound → HCID 10332107, compound

HRID 1788898Notes

Reaction equation

HRID 1788898 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-])=O>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 13423628HCID 13423628, compound

Product 1

HCID 10332107HCID 10332107, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

49.6 g (0.18 mol) of ethyl 1-(2-nitrobenzyl)-imidazole-2-carboxylate were hydrogenated in 500 ml of tetrahydrofuran at room temperature under a pressure of 5 bar in the presence of Raney nickel. After the theoretical quantity of hydrogen had been absorbed, the catalyst was suction-filtered off, and the filtrate was evaporated. 37.7 g (85.4% of theory) of ethyl 1-(2-aminobenzyl)-imidazol-2-carboxylate, m.p. 104°-106° C. (m.p. from toluene 105°-107° C.) were obtained.

Workup

  1. customAfter the theoretical quantity of hydrogen had been absorbed
  2. filtrationthe catalyst was suction-filtered off
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1127223cbea3488e85342ef665537ecd
Source dataset
uspto-grants-1987_08
Patent number
US04686219

Reaction notes

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