2-chloro-N-(3,4-difluorophenyl)acetamide → 5,6-Difluorooxindole

HRID 333036Notes

Reaction equation

HRID 333036 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:13])[CH2:11]Cl)[CH:5]=[CH:6][C:7]=1[F:8].[Cl-].[Al+3].[Cl-].[Cl-]>>[F:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[F:1])[NH:9][C:10](=[O:13])[CH2:11]2

Participants

3

Reactant 2

HCID 7358532-chloro-N-(3,4-difluorophenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125852825,6-Difluorooxindole

Procedure

A mixture of N-(3,4-difluorophenyl)chloroacetamide (14 mmol) and aluminum chloride (54 mmol) was stirred and heated to 200-210 deg C. in a silicon oil bath for 4.5 h. On cooling, 40 mL of ice cold hydrochloric acid was added to the reaction mixture. The solid residue was removed by vacuum filtration and purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent. The yield for this step was 40.7%. 1HNMR (300 MHz, in DMSO-d6) δ 10.46 (s, 1H, NH), 7.33 (t, J=8.7 Hz, 1H, Ar—H), 6.82 (q, J=6.9 Hz, 1H, Ar—H), 3.47 (s, 2H, ArCH2CO).

Workup

  1. temperatureheated to 200-210 deg C
  2. temperatureOn cooling
  3. customThe solid residue was removed by vacuum filtration
  4. custompurified by column chromatography with hexane-ethyl acetate (1:1)
  5. washas eluting solvent
  6. customThe yield for this step

Sources & evidence

ORD record
ord-87b72d0d0a474ec1a5c5d5a7607c2ea2
Source dataset
uspto-grants-2014_11
Patent number
US08877946B2

Reaction notes

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