2,4-Difluoronitrobenzene → 5-Fluoro-N-(1-(3,5-dimethoxyphenyl)ethyl)-2-nitrobenzenamine

HRID 1910539Notes

Reaction equation

HRID 1910539 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:13])[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].C(N(CC)C(C)C)(C)C>C(#N)C>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([NH:13][CH:11]([C:5]2[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:12])[CH:20]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 135102551-(3,5-Dimethoxyphenyl)ethanamine

Product 1

HCID 587073375-Fluoro-N-(1-(3,5-dimethoxyphenyl)ethyl)-2-nitrobenzenamineYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3,5-Dimethoxyphenyl)ethanamine (670 mg, 4.2 mmol), 2,4-difluoronitrobenzene (764 mg, 4.2 mmol) and N,N-diisopropylethylamine (1.08 mg, 8.4 mmol) were stirred at room temperature in dry acetonitrile (50 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 (820 mg, 61% yield). 1H NMR (400 MHz, CDCl3): δ 8.49 (s, 1H), 8.19 (m, 1H), 6.45 (s, 2H), 6.30 (m, 3H), 4.48 (m, 1H), 3.76 (s, 6H), 1.62 (d, 3H); MS (ESI) m/z: Calculated for C16H17FN2O4: 320.12; Observed: 343.2 (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-6abbbd71d97d449a8da1414f0c999974
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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