1-Fluoro-2-nitrobenzene → HCID 14054679, compound

HRID 1722716Notes

Reaction equation

HRID 1722716 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[O:10][CH3:11])[CH2:5][NH:6][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 517165Ammonium AcetateHCID 14054678HCID 14054678, compound

Product 1

HCID 14054679HCID 14054679, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,5-dichloro-4-methoxybenzylamine (6 g, 29.2 mmole), 2-fluoronitrobenzene (2 g, 14.2 mmole) and ammonium acetate (1.0 g) was heated at 80° for 1 hour. The cooled mixture was taken up into ethyl acetate and washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine, dried (Na2SO4), and concentrated to give the title compound 4.0 g (78%) as orange crystals, mp 128°.

Workup

  1. temperaturewas heated at 80° for 1 hour
  2. washwashed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5703498cf2c9497d879feb5e803accff
Source dataset
uspto-grants-1989_08
Patent number
US04857540

Reaction notes

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