Reaction #155328

Reaction equation

sodium hydroxide

ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate

→

[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetic acid

Yield 88.4%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureheated for 2 hours
2. 2
   Temperatureunder reflux
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   TemperatureWhile ice-cooling the concentrate, water and concentrated hydrochloric acid
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   OtherSubsequently, the formed insoluble matter was separated
7. 7
   Otherdried

Procedure

A 5N aqueous sodium hydroxide solution (10 ml) was added to an ethanol solution (30 ml) of ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate (700 mg, 1.55 mmol) and heated for 2 hours under reflux. The mixture was cooled to room temperature and concentrated under reduced pressure. While ice-cooling the concentrate, water and concentrated hydrochloric acid were added to the residue to make it acidic. Subsequently, the formed insoluble matter was separated and dried, giving a yellow powder of [3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetic acid (580 mg, yield: 88%).

Source