Ethyl Acetate → 2-(4-Chlorophenyl)ethylamine

HRID 1843817Notes

Reaction equation

HRID 1843817 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][N+:10]([O-])=O)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC(=O)C)C>C1COCC1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 95339p-Chloro-beta-nitrostyreneHCID 21226445Aluminium lithium hydride

Product 1

HCID 674302-(4-Chlorophenyl)ethylamineYield 90,307.398%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
45 °C

Procedure

1-Chloro-4-(2-nitro-vinyl)-benzene (I-1a: 3.4 g, 0.0185 mmol) dissolved in dry THF (50 mL) was added dropwise to a stirred suspension of LAH (1.3 g, 0.03707 mmol) in dry THF (50 mL) over a period of 20 minutes at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at 45° C. for 3 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was cooled to room temperature, quenched with 10% NaOH solution (3 mL), and filtered through Celite® bed. The filtrate was washed with ethylacetate and concentrated under reduced pressure to afford 2.6 g of the crude product which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with 10% NaOH solution (3 mL)
  3. filtrationfiltered through Celite® bed
  4. washThe filtrate was washed with ethylacetate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d55ad68bf3c49c6885bcca687b755bb
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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