Hydrochloric Acid → 2-Amino-5-(4-methoxypyridin-2-yl)benzimidazole dihydrochloride

HRID 1060026Notes

Reaction equation

HRID 1060026 reaction equation
[C:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[N+:18]([O-])=O)#[N:2].[ClH:21]>C(O)C.C(OCC)(=O)C.O1CCOCC1.[Ni]>[ClH:21].[ClH:21].[NH2:2][C:1]1[NH:18][C:5]2[CH:6]=[C:7]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 18667498N-cyano-4-(4-methoxypyridin-2-yl)-2-nitroaniline

Product 1

HCID 186676092-Amino-5-(4-methoxypyridin-2-yl)benzimidazole dihydrochloride

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of N-cyano-4-(4-methoxypyridin-2-yl)-2-nitroaniline (200 mg) in ethanol (10 ml) was hydrogenated over Raney-nickel (500 mg) under a hydrogen atmosphere for 12 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 20 g, dichloromethane:methanol:aqueous ammonia=100:10:1). The compound obtained was dissolved in ethyl acetate, and a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) was added. The precipitate was collected by filtration and dried to give 2-amino-5-(4-methoxypyridin-2-yl)benzimidazole dihydrochloride (142 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 20 g, dichloromethane:methanol:aqueous ammonia=100:10:1)
  4. customThe compound obtained
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c6ed7ea49928435a8d53e9e4aa360a52
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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