Ammonium Chloride → (4-Chloroquinolin-3-yl)methanol

HRID 576964Notes

Reaction equation

HRID 576964 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH:12]=[O:13].[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14780304-chloroquinoline-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 224397(4-Chloroquinolin-3-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 4-chloroquinoline-3-carbaldehyde (1.2 g, 6.3 mmol) in anhydrous methanol (20 mL) was added sodium borohydride (250 mg, 6.6 mmol). The reaction mixture was stirred at room temperature for 3 hours. Saturated ammonium chloride solution (20 mL) was added. The resultant mixture was extracted with dichloromethane (2×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (4-chloroquinolin-3-yl)methanol (1.0 g, 85% yield). The product was used without further purification.

Workup

  1. extractionThe resultant mixture was extracted with dichloromethane (2×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ce9a82bdb57f45488d67c1fa50bcee54
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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