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

HRID 2197434Notes

Reaction equation

HRID 2197434 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-415ab69707b646358d578f706e879008
Source dataset
uspto-grants-2012_12
Patent number
US08338590B2

Reaction notes

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