Methanol → HCID 54320756, compound

HRID 1291049Notes

Reaction equation

HRID 1291049 reaction equation
[C:1]1([C:7]2[N:8]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#N)=[CH:14][CH:13]=3)[CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[NH4+].[Cl-].[BH4-].[Na+].C[OH:35]>ClCCl.C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]([C:12]3[CH:19]=[CH:18][C:15]([CH2:16][OH:35])=[CH:14][CH:13]=3)[CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 25517Ammonium Chloride2×HCID 4311764Sodium borohydrideHCID 18920171HCID 18920171, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 54320756HCID 54320756, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-phenylimidazol-1-yl)benzonitrile (3.2 g, 13 mmol) in dichloromethane (30 ml) and toluene (20 ml) cooled to -78° C. was added dropwise diisobutylaluminum hydride (13 ml, 13 mmol: 1.02M solution in toluene) under a nitrogen atmosphere and the whole stirred at this temperature for 1.5 h. Saturated aqueous NH4Cl solution (20 ml) was then added carefully to the reaction mixture, and the whole allowed to warm to room temperature. The resulting gelatinous mixture was filtered through a pad of celite, washing with ethyl acetate (200 ml). The filtrate was washed with 0.3N HCl solution (100 ml), water (200 ml) and brine (100 ml), and the organic layer dried over MgSO4. Removal of solvent under reduced pressure provided crude product (2.5 g) which was dissolved in methanol (30 ml) and cooled to 0° C. NaBH4 (0.3 g, 8 mmol) was added in portions and the reaction mixture stirred for 30 min. Saturated aqueous NH4Cl solution (30 ml) was added to the reaction mixture and the whole extracted with ethyl acetate (20 ml×3). The organic layer was washed with water (10 ml), brine (10 ml), dried over MgSO4 and solvent removed under reduced pressure. The resultant crude product was washed with ethyl acetate (35 ml) to give the title compound (0.81 g, 25%) as a white powder.

Workup

  1. filtrationThe resulting gelatinous mixture was filtered through a pad of celite
  2. washwashing with ethyl acetate (200 ml)
  3. washThe filtrate was washed with 0.3N HCl solution (100 ml), water (200 ml) and brine (100 ml)
  4. dry with materialthe organic layer dried over MgSO4
  5. customRemoval of solvent under reduced pressure
  6. customprovided crude product (2.5 g) which
  7. temperaturecooled to 0° C
  8. stirringthe reaction mixture stirred for 30 min
  9. extractionthe whole extracted with ethyl acetate (20 ml×3)
  10. washThe organic layer was washed with water (10 ml), brine (10 ml)
  11. dry with materialdried over MgSO4 and solvent
  12. customremoved under reduced pressure
  13. washThe resultant crude product was washed with ethyl acetate (35 ml)

Sources & evidence

ORD record
ord-924532b181144f78921a5f2c98d57082
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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