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

HRID 2258514
Notes
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Reaction equation

HRID 2258514 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 229221457-Chloro-2-(5-formylbenzofuran-2-yl)quinoline

Product 1

HCID 229221977-Chloro-2-(5-hydroxymethylbenzofuran-2-yl)quinolineYield 87.5%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6212ChloroformSolvent

Procedure

To a cooled solution of 7-chloro-2-(5-formylbenzofuran-2-yl)quinoline (0.92 g) in a mixture of methanol (20 ml) and chloroform (10 ml) was added sodium borohydride (0.40 g) in small portions. After being stirred at the same temperature for 2 hours, the resulting mixture was treated with diluted hydrochloric acid and adjusted to be basic with aqueous sodium hydrogen carbonate. The resulting precipitates were collected by filtration, Washed with water and dried to give 7-chloro-2-(5-hydroxymethylbenzofuran-2-yl)quinoline (0.81 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washWashed with water
  4. customdried

Sources & evidence

ORD record
ord-b55952b059ce49779fe5ab79b2cde8a8
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05661159

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes