Potassium Hydroxide → HCID 86741891, compound

HRID 247380Notes

Reaction equation

HRID 247380 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[C:4]([C:15]([O:17]C)=[O:16])=[CH:3][CH:2]=1.[OH-].[K+]>CO>[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[C:4]([C:15]([OH:17])=[O:16])=[CH:3][CH:2]=1.[CH2:5]([O:6][CH2:7][CH3:8])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14031270Methyl 10H-phenoxazine-4-carboxylate

Product 1

HCID 86741891HCID 86741891, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl phenoxazine-4-carboxylate (0.241 g, 1 mmol) in methanol (25 ml) containing potassium hydroxide (0.560 g) was heated at reflux for 1 hour. The solvent was removed in vacuo and 5% hydrochloric acid added to the residue. The product was extracted with ethyl acetate, washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. The solid residue was homogeneous by TLC over silica gel (ethyl acetate:hexane 1:3) and was different from the monocarboxylic acid described by Gilman and Moore. After recrystallization from benzene:ethyl ether phenoxazine-4-carboxylic acid, mp 181°-182° C. was obtained.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed in vacuo and 5% hydrochloric acid
  4. additionadded to the residue
  5. extractionThe product was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed under reduced pressure
  9. customAfter recrystallization from benzene

Sources & evidence

ORD record
ord-f3b15d68b99e45c68916ea7eb650c3dc
Source dataset
uspto-grants-1987_11
Patent number
US04707473

Reaction notes

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