Water → 3-(2,5-Difluorophenylamino)propan-1-ol

HRID 1712608Notes

Reaction equation

HRID 1712608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=O)[CH2:11][CH2:12][OH:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68503422N-(2,5-difluorophenyl)-3-hydroxypropionamide

Product 1

HCID 616690273-(2,5-Difluorophenylamino)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.185 g of N-(2,5-difluorophenyl)-3-hydroxypropionamide in 3 ml of tetrahydrofuran is added dropwise at room temperature to a suspension of 0.074 g of lithium aluminium hydride in 6 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature over 12 hours and subsequently hydrolysed with 0.13 ml of water followed by 0.13 ml of 1M NaOH. The mixture is filtered through Hyflo and the filtrate is washed with 10 ml of brine. The organic phase is dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow liquid from the residue by means of flash chromatography (SiO2 60F). Rf=0.28 (1:1 EtOAc-heptane); Rt=3.39.

Workup

  1. filtrationThe mixture is filtered through Hyflo
  2. washthe filtrate is washed with 10 ml of brine
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bd89073a105241a4b6684fa6cb7d29d0
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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