Ethyl 1-methyl-4-nitroimidazole-2-carboxylate → ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

HRID 908137Notes

Reaction equation

HRID 908137 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[N:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H][H]>CCO.C(OCC)(=O)C.[Pd]>[NH2:7][C:5]1[N:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:2]([CH3:1])[CH:6]=1

Participants

5

Reactant 2

HCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 7006687ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Im-2 (0.4 g) in EtOH/ethyl acetate (1:1, 14 mL) and Pd/C (10%, 0.3 g) were stirred under a slight positive pressure of hydrogen (ca 1.1 atm) for 3-4 hr. The reaction mixture was filtered using celite and solvent evaporated on the rotary. The remaining solid was freeze dried to yield a slightly yellow product. Yield (0.38 g, 95%). 1H NMR (DMSO): δ 6.45 (s, 1H), 4.5 (bs, 2H, NH2), 4.2 (q, 2H, J=7 Hz), 3.76 (s, 3H), 1.24 (t, 3H, J=7.9 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated on the rotary
  3. customdried
  4. customto yield a slightly yellow product
  5. customYield (0.38 g, 95%)

Sources & evidence

ORD record
ord-339bc87b5ff7413fa47393e3a65baa34
Source dataset
uspto-grants-2011_09
Patent number
US08017599B2

Reaction notes

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