Water → HCID 23706966, compound

HRID 2418357Notes

Reaction equation

HRID 2418357 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:20].[Na+:21].O>O1CCOCC1>[NH2:3][C:4]1[C:5]([O:11][C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([O-:20])=[O:1].[Na+:21]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 20446181HCID 20446181, compound

Product 1

HCID 23706966HCID 23706966, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-oxo-7-(2,6-dichlorophenoxy)indoline (3.4 g.), sodium hydroxide (1.86 g.) and water (50 ml.) was refluxed under heating for 120 hours with stirring. Insoluble starting material (2.5 g.) was recovered by filtration and the filtrate was cooled. The precipitates were collected by filtration and washed with a small amount of water and diethyl ether in turn to give the captioned compound (1.35 g.). Further, to the above obtained insoluble material (2.5 g.) were added sodium hydroxide (2 g.) and 50% dioxane (50 ml.), and the mixture was stirred for 70 hours and filtered. After cooling, the precipitates were collected by filtration and washed with water and diethyl ether in turn to give the same captioned compound (1.3 g.). Total yield (2.65 g.). mp>230° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 120 hours
  3. filtrationwas recovered by filtration
  4. temperaturethe filtrate was cooled
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with a small amount of water and diethyl ether in turn
  7. customto give the captioned compound (1.35 g.)
  8. stirringthe mixture was stirred for 70 hours
  9. filtrationfiltered
  10. temperatureAfter cooling
  11. filtrationthe precipitates were collected by filtration
  12. washwashed with water and diethyl ether in turn
  13. customto give the same captioned compound (1.3 g.)
  14. customTotal yield (2.65 g.)

Sources & evidence

ORD record
ord-fc11f04137304708b018cf4fd480b99b
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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