Water → 4-Chloro-N-[(1H-imidazol-2-yl)methyl]aniline

HRID 1179437Notes

Reaction equation

HRID 1179437 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[BH4-].[Na+].O>CO>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH2:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78124-ChloroanilineHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 108460134-Chloro-N-[(1H-imidazol-2-yl)methyl]anilineYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 2-imidazolecarboxaldehyde (570 mg, 5.9 mmol) and 4-chloroaniline (756 mg, 5.9 mmol) in methanol (5 ml) was stirred at 60° C. for 4 hours, and allowed to cool to room temperature. To the reaction was added NaBH4 (337 mg, 8.9 mmol), and the mixture was additionally stirred for an hour. Water (20 mL) was added to the reaction, which was extracted with ethyl acetate (50 mL). Organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol in chloroform) to give the title compound (660 mg, 53%).

Workup

  1. extractionwas extracted with ethyl acetate (50 mL)
  2. dry with materialOrganic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5% methanol in chloroform)

Sources & evidence

ORD record
ord-813eb3b18b5d45a98cf056db46d03476
Source dataset
uspto-grants-2007_10
Patent number
US07279497B2

Reaction notes

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