Formic Acid → 3-(4-Methyl-1H-imidazol-1-yl)benzenamine

HRID 1461920Notes

Reaction equation

HRID 1461920 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[CH:6]=1.C([O-])=O.[Na+].C(O)=O>CO.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723810Sodium FormateHCID 150301664-methyl-1-(3-nitrophenyl)-1H-imidazole

Product 1

HCID 150301673-(4-Methyl-1H-imidazol-1-yl)benzenamineYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 14.6 g of 4-methyl-1-(3-nitrophenyl)-1H-imidazole, 766 mg of palladium black, 19.6 g of sodium formate, 12.8 ml of formic acid in 300 ml of methyl alcohol is stirred for 18 hours under a hydrogen atmosphere. The mixture is filtered through diatomaceous earth and the filtrate evaporated to a residue. The residue is partitioned between saturate potassium bicarbonate and chloroform. The organic layer is dried and evaporated to a residue which is dissolved in a minimum of chloroform and passed through a pad of hydrous magnesium silicate. The filtrate is evaporated to a residue which is stirred with ether and the resulting solid filtered and air dried to give 10.3 g of the desired product as a solid, m.p. 117°-119° C.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. customthe filtrate evaporated to a residue
  3. customThe residue is partitioned
  4. concentrationbetween saturate potassium bicarbonate and chloroform
  5. customThe organic layer is dried
  6. customevaporated to a residue which
  7. dissolutionis dissolved in a minimum of chloroform
  8. customThe filtrate is evaporated to a residue which
  9. stirringis stirred with ether
  10. filtrationthe resulting solid filtered
  11. customair dried

Sources & evidence

ORD record
ord-dbd2f11aee69470a843d0f38a84286c7
Source dataset
uspto-grants-1991_12
Patent number
US05077409

Reaction notes

Loading…