Sodium Hydroxide → HCID 23706986, compound

HRID 2418391Notes

Reaction equation

HRID 2418391 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:18])[CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:3]1.[OH-:19].[Na+:20]>O.O1CCOCC1>[NH2:3][C:4]1[C:5]([Cl:18])=[CH:6][CH:7]=[C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]=1[CH2:10][C:2]([O-:19])=[O:1].[Na+:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20446293HCID 20446293, compound

Product 1

HCID 23706986HCID 23706986, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-oxo-4-phenoxy-7-chloroindoline (4.2 g) and sodium hydroxide (1.3 g) in water (40 ml) and dioxane (10 ml) was refluxed for 24 hrs. After cooling, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in ethanol under heating, and the solution was filtered. The filtrate was allowed to stand under ice-cooling, and the precipitating crystals were collected by filtration, washed with ethanol and dried to give sodium 2-(2-amino-3-chloro-6-phenoxyphenyl)acetate (1.8 g). The same product (2.3 g) was obtained from the mother liquid. Total yield 4.1 g. mp>240° C.

Workup

  1. temperaturewas refluxed for 24 hrs
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethanol
  6. temperatureunder heating
  7. filtrationthe solution was filtered
  8. temperaturecooling
  9. filtrationthe precipitating crystals were collected by filtration
  10. washwashed with ethanol
  11. customdried

Sources & evidence

ORD record
ord-49b912258b414e45b2ef78908fea34cd
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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