Water → HCID 10999569, compound

HRID 1199996Notes

Reaction equation

HRID 1199996 reaction equation
C([O:3][C:4]([C:6]1[CH:22]=[CH:21][C:9]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[N:13]=[C:12]2[CH3:20])=[CH:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Cl-].[NH4+]>O1CCCC1>[OH:3][CH2:4][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[N:13]=[C:12]2[CH3:20])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 18958960HCID 18958960, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10999569HCID 10999569, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Ethoxycarbonylbenzyl)-2-methylimidazo[4,5-c]pyridine (2.0 g) was suspended in tetrahydrofuran (50 ml) under N2 and lithium aluminium hydride (0.16 g) was added portionwise over 5 minutes. The mixture was stirred at room temperature for 1 hour and then water was added cautiously, followed by saturated ammonium chloride solution. The mixture was extracted with ethyl acetate (3×50 ml) and the combined extracts were dried over Na2SO4, filtered and evaporated under vacuum. The residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol and the fractions containing the product were evaporated to yield the title compound, (0.64 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol
  6. additionthe fractions containing the product
  7. customwere evaporated

Sources & evidence

ORD record
ord-c19ef81bcb064f84809df5158a011c11
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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