Sodium Hydroxide → HCID 58492449, compound

HRID 68146Notes

Reaction equation

HRID 68146 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:21]2[C:12](=[C:13]3[C:18](=[CH:19][C:20]=2[O:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16][CH2:15][O:14]3)[C:11](=[O:26])[C:10]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:9]1)C>C(O)C>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:10]2[C:11](=[O:26])[C:12]3[C:21](=[C:20]([O:22][CH2:23][CH2:24][CH3:25])[CH:19]=[C:18]4[C:13]=3[O:14][CH2:15][CH2:16][CH2:17]4)[N:8]([CH2:7][C:6]([OH:35])=[O:5])[CH:9]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58492458HCID 58492458, compound

Product 1

HCID 58492449HCID 58492449, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. temperatureheated for 2 hours
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. temperatureWhile ice-cooling the concentrate, water and concentrated hydrochloric acid
  5. additionwere added to the residue
  6. customSubsequently, the formed insoluble matter was separated
  7. customdried

Sources & evidence

ORD record
ord-f82ee64e6eac474c829047afbda65bed
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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