1-Methyl-2-(2-nitrophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal → Benzenamine, 2-[4-(1,3-dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl]-

HRID 843234Notes

Reaction equation

HRID 843234 reaction equation
[CH2:1]1[O:24][CH:4]([C:5]2[C:13]3[N:12]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-])=O)[N:10]([CH3:23])[C:9]=3[CH:8]=[CH:7][CH:6]=2)[O:3][CH2:2]1>CO.[Pd]>[CH2:1]1[O:24][CH:4]([C:5]2[C:13]3[N:12]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[NH2:20])[N:10]([CH3:23])[C:9]=3[CH:8]=[CH:7][CH:6]=2)[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 154902661-Methyl-2-(2-nitrophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal

Product 1

HCID 11346961Benzenamine, 2-[4-(1,3-dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl]-Yield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6 (0.85 g, 2.6 mmol) in 50 mL MeOH was mixed with 85 mg of Pd/C and hydrogenated with H2 at a pressure of 10 psi for 3 hours. The mixture was then filtered, and the solvent was removed to give 0.76 g (98%) of the title compound as a white solid. 1H NMR (CDCl3): δ 4.44 (s, 3H), 4.69-4.90 (m, 4H), 5.69 (broad s, 2H), 7.44 (d, J=7.8 Hz, 2H), 7.81-8.05 (m, 4H), 8.14 (d, J=1.6, 6.9 Hz, 1H); HRMS: Calcd. for C17H17N3O2 295.1321, found 295.1325.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-0324657e1c18428c935804c2c4abdf3e
Source dataset
uspto-grants-2002_04
Patent number
US06376664B1

Reaction notes

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