Aluminum(III) Chloride → HCID 11738308, compound

HRID 603353Notes

Reaction equation

HRID 603353 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl: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-]>>[Cl:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[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

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 11279335HCID 11279335, compound

Product 1

HCID 11738308HCID 11738308, compound

Conditions

Temperature
165 °C

Procedure

A mixture of 6.85 g (20 mmol) of N-(2′,6′-dichloro-4′-methylphenyl)-N-chloroacetyl-4-methylaniline and 3.36 g (26 mmol) of aluminium chloride was heated slowly to 160-170° C. and held at this temperature for 3-4 h. During this time, nitrogen was continuously bubbled into the melt. The mixture was diluted with 20 ml of toluene and added on 20 ml of warm water. The organic layer was separated, washed with water and evaporated. The residue was crystallised from 20 ml of 2-propanol giving N-(2′,6′-dichloro-4′-methylphenyl)-5-methyloxindole. Mp: 153-154° C.

Workup

  1. customDuring this time, nitrogen was continuously bubbled into the melt
  2. additionThe mixture was diluted with 20 ml of toluene
  3. additionadded on 20 ml of warm water
  4. customThe organic layer was separated
  5. washwashed with water
  6. customevaporated
  7. customThe residue was crystallised from 20 ml of 2-propanol

Sources & evidence

ORD record
ord-3dafce3cb35e48d885cb49f50e1b31d2
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

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