Formic Acid → 4-(2-methyl-1H-imidazol-1-yl)aniline

HRID 483573

Reaction equation

HRID 483573 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.C([O-])=O.[Na+].C(O)=O>CO.[Pd]>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723810Sodium FormateHCID 100131182-Methyl-1-(4-nitrophenyl)-1H-imidazole

Product 1

HCID 31574784-(2-methyl-1H-imidazol-1-yl)anilineYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 54.0 g of 2-methyl-1-(p-nitrophenyl)imidazole, 2.87 g of palladium black, 36.7 g of sodium formate and 47.4 ml of formic acid in 1100 ml of methyl alcohol is stirred at room temperature for 18 hours under a hydrogen atmosphere. The mixture is filtered and the filtrate evaporated to a residue. The residue is partitioned between saturated potassium bicarbonate and chloroform. The organic layer is dried and passed through a pad of hydrous magnesium silicate. The filtrate is evaporated to a residue which is crystallized from ether:ethanol to give 34.9 g of the desired product as a solid, m.p. 108°-110° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated to a residue
  3. customThe residue is partitioned between saturated potassium bicarbonate and chloroform
  4. customThe organic layer is dried
  5. customThe filtrate is evaporated to a residue which
  6. customis crystallized from ether

Sources & evidence

ORD record
ord-62bbf20c3e1e4af38a3f7fff08dd1660
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Linked notes

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