Methanol → HCID 15224433, compound

HRID 274390Notes

Reaction equation

HRID 274390 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:17][C:18](=[O:20])[CH3:19].[BH4-].[Na+].CO.O>C(O)C>[CH3:19][CH:18]([OH:20])[CH2:17][C:5]1[N:4]([CH2:3][CH:2]([CH3:21])[CH3:1])[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 15224432HCID 15224432, compound

Product 1

HCID 15224433HCID 15224433, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]propan-2-one (8 g, 28.4 mmol, Example 73) was suspended in ethanol (400 mL). Sodium borohydride (1.64 g, 43.3 mmol) was added and the reaction mixture was stirred at room temperature for about 2 hours. Methanol (about 20 mL) was added and stirring was continued over night. Water was added then the solvents were removed under vacuum. The residue was partitioned between methylene chloride and water. The methylene chloride layer was separated, dried over magnesium sulfate then concentrated under vacuum to give the desired product. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. stirringstirring
  2. waitwas continued over night
  3. customthe solvents were removed under vacuum
  4. customThe residue was partitioned between methylene chloride and water
  5. customThe methylene chloride layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-58c62d9a500d4ad9a5d2fded949da925
Source dataset
uspto-grants-1995_02
Patent number
US05389640

Reaction notes

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