Ammonium Chloride → HCID 69810525, compound

HRID 1959756Notes

Reaction equation

HRID 1959756 reaction equation
[F:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[BH4-].[Na+].[NH4+].[Cl-]>CO>[F:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 579172825,7-Difluoroquinoline-6-carbaldehyde

Product 1

HCID 69810525HCID 69810525, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5,7-difluoroquinoline-6-carbaldehyde (4.00 g, 20.71 mmol) in MeOH (120 mL), was added NaBH4 (0.79 g, 20.71 mmol) in portions. After stirring for 15 min, saturated aqueous solution of NH4Cl was added. The aqueous phase was extracted with CH2Cl2 (4×25 mL). The organic layers were combined and dried over NaSO4. The product was purified by silica gel with hexane:EtOAc to afford (5,7-difluoroquinolin-6-yl)methanol (3.80 g, 94%). NMR (400 MHz, CDCl3) δ ppm 8.97 (m, 1H), 8.42 (m, 1H), 7.63 (d, 1H), 7.46 (m, 1H), 4.99 (d, 2H), 2.07 (t, 1H). LCMS (method B): [MH]+=196.0, tR=1.67 min

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (4×25 mL)
  2. dry with materialdried over NaSO4
  3. customThe product was purified by silica gel with hexane

Sources & evidence

ORD record
ord-f696a2fd41a44c52a6be9f9ab97485a8
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

Loading…