2-(2-Chloro-4-fluorophenyl)acetamide → 2-(2-Chloro-4-fluorophenyl)ethan-1-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH2:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield).
Workup
- temperaturethe reaction was refluxed for 3 hours
- temperatureThe reaction was cooled to 0° C.
- customquenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water
- filtrationwas filtered
- concentrationconcentrated
- customThe material was purified
- washeluting with 2% NH4OH/10% methanol/DCM
Sources & evidence
- ORD record
- ord-831d5b2a77864753bfaa346b756966fc
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569522B2
Reaction notes
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