Aniline → Acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl ester

HRID 243250Notes

Reaction equation

HRID 243250 reaction equation
F[C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([F:16])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[F:16][C:9]1[C:3]([CH2:4][O:5][C:6](=[O:8])[CH3:7])=[C:2]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 68157040Acetic acid 2,6-difluoro-3-nitrobenzyl ester

Product 1

HCID 68156961Acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl esterYield 81.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of acetic acid 2,6-difluoro-3-nitrobenzyl ester (3 g, 12.9 mmol) and aniline (1.5 mL, 16.9 mmol) in DMSO (10 mL) was heated at 100° C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc (3×15 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to give the title compound as a brown oil (3.2 g, 81%). 1H NMR 400 MHz 6 (CDCl3): 8.21 (1H, dd, J=9.4, 5.9 Hz), 7.30-7.24 (2H, m), 7.10-7.04 (1H, m), 6.97-6.92 (2H, m), 6.83 (1H, dd, J=9.3, 8.4), 4.93 (2H, d, J=2.0 Hz), 1.94 (3H, s)

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-fc3e5b5cdf224fada5af251ee859be9c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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