Water → 3-Amino-5-chloro-1,3-dihydro-3-(2-methoxyphenyl)indol-2-one

HRID 552305Notes

Reaction equation

HRID 552305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2(O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19]CC.[NH3:23].C(O)C.O>C(Cl)Cl>[NH2:23][C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]1=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 574664415-Chloro-3-hydroxy-3-(2-propoxyphenyl)-indole-2-one

Product 1

HCID 219254143-Amino-5-chloro-1,3-dihydro-3-(2-methoxyphenyl)indol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (32.45 mmol) of the intermediate product 2a were suspended in 100 ml methylene chloride. After the addition of 100 ml 2-molar ethanol ammonia solution, the reaction mixture was stirred for 16 h. After this, everything was poured on to icy water and the organic phase was separated. The aqueous phase was cooled, wherein a white crystallizate formed, which was isolated. 5.7 g of the product were obtained.

Workup

  1. customthe organic phase was separated
  2. temperatureThe aqueous phase was cooled, wherein a white crystallizate
  3. customformed
  4. customwhich was isolated

Sources & evidence

ORD record
ord-4b674444487e4431b31cbc0f5c655a05
Source dataset
uspto-grants-2011_05
Patent number
US07951807B2

Reaction notes

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