Acetic Acid → HCID 15562230, compound

HRID 1773523Notes

Reaction equation

HRID 1773523 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][C:4]=1[N+:11]([O-])=O.C(O)(=O)C>ClCCl.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][C:4]=1[NH2:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2444164-ethenyl-1-methoxy-2-nitrobenzene

Product 1

HCID 15562230HCID 15562230, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methoxy-2-nitro-4-vinyl-benzene (100 mg) in dichloromethane (2 mL) was added zinc dust (large excess), followed by acetic acid (0.5 mL) and the resulting mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with dichloromethane and discarded. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (hexane/EtOAc, 90/10) to give 50 mg of 2-methoxy-5-vinyl-phenylamine.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-822a2dd495af4a07b19ef92438bff811
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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