2,4-Difluoronitrobenzene → N-(1-(3-Chlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

HRID 2425977Notes

Reaction equation

HRID 2425977 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.F[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 50061701-(3-Chlorophenyl)ethan-1-amine

Product 1

HCID 58707308N-(1-(3-Chlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamineYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Chlorophenyl)ethanamine (553 mg, 3.55 mmol), 2,4-difluoronitrobenzene (565 mg, 3.55 mmol) and N,N-diisopropylethylamine (918 mg, 7.10 mmol) were stirred at room temperature in dry acetonitrile (20 mL) for 6 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated to collect the title compound (600 mg, 57% yield). 1H NMR (400 MHz, CDCl3): δ 8.49 (s, 1H), 8.23 (m, 1H), 7.04 (m, 4H), 6.36 (t, 1H), 6.22 (d, 1H), 4.56 (m, 1H), 1.64 (d, 3H); MS (ESI) m/z: Calculated for C14H13ClFN2O2: 295.06; Observed: 295.0 (M++1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated

Sources & evidence

ORD record
ord-4d6626036dcf435384e85a0790891827
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

Loading…