Sodium Hydroxide → HCID 23706979, compound

HRID 2418378Notes

Reaction equation

HRID 2418378 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[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[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([O-:20])=[O:1].[Na+:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20446239HCID 20446239, compound

Product 1

HCID 23706979HCID 23706979, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-oxo-7-(2-methoxyphenoxy)indoline (2.7 g) and sodium hydroxide (2.1 g) in water (30 ml) and dioxane (30 ml) was refluxed with stirring for 30 hrs. The reaction mixture was concentrated in vacuo, and the residue was dissolved in water and filtered. The filtrate was washed with diethyl ether, neutralized with 5% sulfuric acid and extracted with diethyl ether. The extract was washed with saline, dried over magnesium sulfate and then evaporated in vacuo. The residue was treated with an aqueous solution of sodium bicarbonate, and the resultant oily substance (3.0 g) was crystallized by treating with ethyl acetate to give crystalline sodium 2-[2-amino-3-(2-methoxyphenoxy)phenyl]acetate (1.55 g). mp 101°-103° C. I.R. (NaCl, Nujol): 3500, 3400, 1615, 1600, 1580, 1500, 1470, 1390, 1310, 1265, 1200 cm-1.

Workup

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. filtrationfiltered
  5. washThe filtrate was washed with diethyl ether
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with saline
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. additionThe residue was treated with an aqueous solution of sodium bicarbonate
  11. customthe resultant oily substance (3.0 g) was crystallized
  12. additionby treating with ethyl acetate

Sources & evidence

ORD record
ord-13b32b735bda4a50bb50979761462420
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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