Ammonium formate → HCID 15896318, compound

HRID 381386Notes

Reaction equation

HRID 381386 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-])=O)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.C(OC(=O)C)C.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]=[N:10][C:11]=2[C:16]=1[CH3:17]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 158963171h-Benzimidazole-1-carboxylic acid,4-methyl-5-nitro-,1,1-dimethylethyl ester

Product 1

HCID 15896318HCID 15896318, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

5-Amino-1-tert-butoxycarbonyl-4-methylbenzimidzole. To a solution of 8 g of 1-tert-butoxycarbonyl-4-methyl-5-nitrobenzimidazole in 40 mL of methanol and 400 mL of ethylacetate are added 500 mg of 10% palladium-on-carbon and 7.27 g of ammonium formate. The mixture is stirred at 50° C. for 2 hours, then filtered on Celite, with a methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and ethyl acetate. The organic layer is washed with saturated ammonium chloride, dried over magnesium sulfate, filtered and rotary evaporated to afford 5-amino-1-tert-butoxycarbonyl-4-methylbenzimidazole as an off-white solid.

Workup

  1. filtrationfiltered on Celite, with a methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe organic layer is washed with saturated ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customrotary evaporated

Sources & evidence

ORD record
ord-b4a3fe1cd93245efa635c23f2025facb
Source dataset
uspto-grants-2001_10
Patent number
US06306877B1

Reaction notes

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