Sodium Hydroxide → 3-Amino-1-(3-chlorophenyl)propan-1-ol

HRID 1809667

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([C:14](=[O:18])[CH2:15][C:16]#[N:17])[CH:11]=[CH:12][CH:13]=1.[OH-].[Na+]>C1COCC1>[NH2:17][CH2:16][CH2:15][CH:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=1)[OH:18]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 60° C. for 3 hours. After cooling to 0° C., a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-1-(3-chloro-phenyl)-propan-1-ol obtained was used in the next step without further purification. (Yield 14.5 g, crude).

Workup

temperatureheated at 60° C. for 3 hours
temperatureAfter cooling to 0° C.
extractionextracted with ethyl acetate (200 mL)
dry with materialThe solution was dried over anhydrous sodium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-b8ab23ae0250423fa922e59857b9c465
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362023B2

Linked notes

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