Sodium Hydroxide → HCID 20446174, compound

HRID 2418381Notes

Reaction equation

HRID 2418381 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:22].[Na+]>O1CCOCC1.O>[NH2:3][C:4]1[C:5]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:22])=[O:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20446252HCID 20446252, compound

Product 1

HCID 20446174HCID 20446174, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-oxo-7-(β-naphthoxy)indoline (5 g) and sodium hydroxide (1.6 g) in dioxane (40 ml) and water (80 ml) was refluxed with stirring for 72 hrs. After cooling, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in hot ethanol and filtered. The filtrate was evaporated in vacuo, and ethyl acetate was added to the residue. The resultant ethyl acetate solution was heated. The precipitating crystals were collected by filtration and recrystallized from ethanol to give 2-[2-amino-3-(β-naphthoxy)phenyl]acetic acid (2.9 g). This substance was dissolved in an aqueous sodium bicarbonate, and the solution was filtered and lyophilized to give sodium 2-[2-amino-3-(β-naphtoxy)phenyl]acetate (2.8 g).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved in hot ethanol
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo, and ethyl acetate
  8. additionwas added to the residue
  9. temperatureThe resultant ethyl acetate solution was heated
  10. filtrationThe precipitating crystals were collected by filtration
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5d1e8f7283d54214b756d7e82656154b
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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