Water → 3,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one

HRID 552304

Reaction equation

HRID 552304 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]2(O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].N1C=CC=CC=1.O>C(Cl)Cl>[Cl:3][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([Cl:5])[CH:7]=2)[NH:11][C:10]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

Product 1

HCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

38 ml (0.518 mol) thionyl chloride were slowly added by drops to 100 g (0.345 mol) of the intermediate product 1a, 56 ml (0.695 mol) pyridine in 1 l methylene chloride at 0° C., and then stirred for approximately 30 minutes more. Then the reaction mixture was poured on to icy water and the organic phase was separated. This organic phase was then washed with water, dried and concentrated in a vacuum. The residue was treated with toluene a number of times and the organic solvent was removed in a vacuum each time. 79 g of the raw product were obtained and further reacted without further cleaning.

Workup

  1. customthe organic phase was separated
  2. washThis organic phase was then washed with water
  3. customdried
  4. concentrationconcentrated in a vacuum
  5. additionThe residue was treated with toluene a number of times
  6. customthe organic solvent was removed in a vacuum each time

Sources & evidence

ORD record
ord-6fd1ca05de294db6a5c76e158bcc37e6
Source dataset
uspto-grants-2011_05
Patent number
US07951807B2

Linked notes

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