Hydrochloric Acid → HCID 131727385, compound

HRID 2108834Notes

Reaction equation

HRID 2108834 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:5]=2[NH:4][C:3]1=[O:13].[ClH:14]>CO.CCOC(C)=O.O.[Pd]>[ClH:14].[NH2:12][CH2:11][C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[C:3](=[O:13])[NH:4][C:5]=2[CH:10]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 28693431HCID 28693431, compound

Product 1

HCID 131727385HCID 131727385, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The suspension of 1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile (1.84 g, 10.6 mmol) in MeOH (30 ml) and 38% HCl aqueous solution (5.0 ml) was treated with 10% Pd—C (500 mg) and the mixture was stirred for 50 hours at room temperature under hydrogen atmosphere (4.0 kgf/cm2). After the filtration to remove Pd—C, the filtrate was evaporated to give the crude residue, which was dissolved in EtOAc/38% HCl aqueous solution/water (30:1:30). After washing the aqueous phase with EtOAc, water was removed under reduced pressure, followed by recrystallization from DCM-MeOH to furnish the title compound as a dark pink colored solid (1.45 g, 64%). 1H NMR (CDCl3): δ 3.27 (3H, s), 3.99 (2H, m), 6.90 (3H, m), 8.42 (2H, brs), 11.1 (1H, s). MS (ESI) m/z 179 (M+H)+.

Workup

  1. filtrationAfter the filtration
  2. customto remove Pd—C
  3. customthe filtrate was evaporated
  4. customto give the crude residue, which
  5. washAfter washing the aqueous phase with EtOAc, water
  6. customwas removed under reduced pressure
  7. customfollowed by recrystallization from DCM-MeOH

Sources & evidence

ORD record
ord-bee3e66ff70943038655ac238a21d580
Source dataset
uspto-grants-2009_04
Patent number
US07514457B2

Reaction notes

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