Sodium Hydroxide → HCID 58492449, compound

HRID 1474534Notes

Reaction equation

HRID 1474534 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:24](=[O:25])[C:23]3[C:14](=[C:15]([O:26][CH2:27][CH2:28][CH3:29])[CH:16]=[C:17]4[C:22]=3[O:21][CH2:20][CH2:19][CH2:18]4)[N:13]([CH2:30][C:31]([O:33]CC)=[O:32])[CH:12]=2)=[CH:7][CH:6]=1>C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:24](=[O:25])[C:23]3[C:14](=[C:15]([O:26][CH2:27][CH2:28][CH3:29])[CH:16]=[C:17]4[C:22]=3[O:21][CH2:20][CH2:19][CH2:18]4)[N:13]([CH2:30][C:31]([OH:33])=[O:32])[CH:12]=2)=[CH:7][CH:6]=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-725e268790e64e28b51414b4c7216a06
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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