Sodium Hydroxide → 2-Amino-1-(3-chlorophenyl)ethan-1-ol

HRID 1186545Notes

Reaction equation

HRID 1186545 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([OH:17])[C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1.[OH-].[Na+]>C1COCC1>[NH2:16][CH2:15][CH:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=1)[OH:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1361658853313-92-1HCID 21226445Aluminium lithium hydride

Product 1

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of LAH (2.36 g, 59 mmol) in dry THF (70 mL) was added a solution of (3-chloro-phenyl)-hydroxy-acetonitrile (4.0 g, 24 mmol) in dry THF (55 mL) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 60° C. for 2 hours. After cooling to 0° C., a saturated solution of sodium hydroxide was added dropwise and extracted with dichloromethane (200 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by column chromatography (methanol:dichloromethane, 1:10) to afford 2-amino-1-(3-chloro-phenyl)-ethanol. (Yield 2.86 g, 70%). LC-MS: [M+H]+ 172.

Workup

  1. temperatureheated at 60° C. for 2 hours
  2. temperatureAfter cooling to 0° C.
  3. extractionextracted with dichloromethane (200 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (methanol:dichloromethane, 1:10)

Sources & evidence

ORD record
ord-0f3487c6d6594fd284aad4a6df9e7f5d
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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