Hydrochloric Acid → 7-Chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline

HRID 2258515Notes

Reaction equation

HRID 2258515 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:13]=[CH:14][C:15]4[O:19][C:18]([C:20](OC)=[O:21])=[CH:17][C:16]=4[CH:24]=3)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:13]=[CH:14][C:15]4[O:19][C:18]([CH2:20][OH:21])=[CH:17][C:16]=4[CH:24]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 229221827-Chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline

Product 1

HCID 229222147-Chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 7-chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline (0.92 g) in tetrahydrofuran (10 ml), lithium aluminum hydride (76.7 mg) was added dropwise under ice cooling. After being stirred for 2 hours, the resulting mixture was poured into a mixture of ice and diluted aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene. The fractions containing object compound were combined, concentrated under reduced pressure, and recrystallized from toluene to give 7-chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline (0.58

Workup

  1. additionwas added dropwise under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of ethyl acetate and toluene
  7. additionThe fractions containing object compound
  8. concentrationconcentrated under reduced pressure
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-988932bb048d42f0970fe16d23392df4
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

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