Hydrochloric Acid → HCID 21938661, compound

HRID 1280856Notes

Reaction equation

HRID 1280856 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N:10]([C:18](=[O:21])[CH2:19]Cl)[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl.Cl>O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N:10]1[C:11]2[C:16](=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:19][C:18]1=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 21938676HCID 21938676, compound

Product 1

HCID 21938661HCID 21938661, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 100 g (0.3 mol) of N-(2′-chloro-4′,6′-difluorophenyl)-N-chloroacetyl-4-methylaniline and 103 g (0.78 mol) of aluminum chloride is added 400 ml of 1,2-dichlorobenzene. The reaction is heated to 140° for 2 hours. The reaction is cooled to room temperature and added to a mixture of 100 ml of concentrated HCl and 700 ml water (cooled to 0-5° in a dry ice/acetone bath). The mixture is extracted twice with 400 ml of methylene chloride. The combined organic layers are washed with 600 ml of 3N HCl. The organic layer is stirred with 66 g of magnesium sulfate and 33 g of charcoal (DARCO G-60). The solids are filtered off and the solvents are evaporated under reduced pressure to give a tan solid which is recrystallized from ethanol to give N-(2′-chloro-4′,6′-difluorophenyl)-5-methyloxindole, mp 137-140°.

Workup

  1. temperatureThe reaction is heated to 140° for 2 hours
  2. extractionThe mixture is extracted twice with 400 ml of methylene chloride
  3. washThe combined organic layers are washed with 600 ml of 3N HCl
  4. filtrationThe solids are filtered off
  5. customthe solvents are evaporated under reduced pressure
  6. customto give a tan solid which
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-ffbd06adcabe4f80bebe12c944ce30c7
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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