Water → HCID 59728236, compound

HRID 2043331Notes

Reaction equation

HRID 2043331 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.[BH4-].[Na+].O>CO>[N:15]1[CH:16]=[C:12]([CH2:10][NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[O:2][CH3:1])[NH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70002-MethoxyanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59728236HCID 59728236, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methoxyaniline (0.62 g, 5 mmol) in methanol (5 ml) was added 4-formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 60° C. the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by recrystallisation from heptane/ethyl acetate to yield off-white crystals (0.85 mg, 84%); MS (ISP): 204.3 ((M+H)+.).

Workup

  1. temperaturewas cooled
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by recrystallisation from heptane/ethyl acetate

Sources & evidence

ORD record
ord-4e44cb8076034506ab356f41dd4c6039
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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