Sodium borohydride → (4-Chloroquinolin-7-yl)methanol

HRID 965000Notes

Reaction equation

HRID 965000 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)=O.[BH4-].[Na+]>CO>[OH:2][CH2:3][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21708520Methyl 4-chloroquinoline-7-carboxylate

Product 1

HCID 22054610(4-Chloroquinolin-7-yl)methanolYield 30.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Methoxycarbonyl-4-chloroquinoline(3.75 g, 0.017 mol) was dissolved in methanol (200 ml), added under ice-cooling with sodium borohydride (12.9 g, 0.34 mol) and stirred for an hour. The reaction mixture was poured into ice water. The resulting precipitates were collected by filtration, dried over phosphorus pentoxide and recrystallized from chloroform (20 ml) to obtain 1.0 g (30%) of 7-hydroxymethyl-4-chloroquinoline.

Workup

  1. additionadded under ice-
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. dry with materialdried over phosphorus pentoxide
  5. customrecrystallized from chloroform (20 ml)

Sources & evidence

ORD record
ord-46de3671617c45bd83848ffcb82be690
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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