HCID 87247295, compound → HCID 21719491, compound

HRID 2367145Notes

Reaction equation

HRID 2367145 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4](/[C:8](=[N:10]\O)/[CH3:9])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.CO.[Zn]>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 87247295HCID 87247295, compound

Product 1

HCID 21719491HCID 21719491, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To (1Z)-1-(3-chloro-2-methylphenyl)ethanone oxime (383 mg, 2.08 mmol) in acetic acid (10 ml) was added zinc dust (2.72 g, 41.6 mmol) and the resulting mixture was stirred at 40° C. for 3 hours. The reaction mixture was diluted with methanol and filtered. The filtrate was concentrated in vacuo and the obtained residue was partitioned between 1 N hydrochloric acid and ethyl acetate. The aqueous portion was neutralized with sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give 1-(3-chloro-2-methylphenyl)ethanamine as a clear oil (290 mg, 1.7 mmol, 82% yield). 1H NMR (400 MHz, CDCl3): 8.98 (s, 1H), 7.11-7.44 (m, 3H), 2.37 (s, 3H), 1.81 (s, 3H); MS (EI) for C9H12ClN: 170 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe obtained residue was partitioned between 1 N hydrochloric acid and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8870b998de34428d86e2c80126b9cd7e
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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