Sodium Hydroxide → 5-Methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid

HRID 26703Notes

Reaction equation

HRID 26703 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]2[CH:14]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:16]=[C:6]2[C:5]1=[O:22]>O.C(O)C>[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]2[CH:14]=[C:15]([C:17]([OH:19])=[O:18])[CH:16]=[C:6]2[C:5]1=[O:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14067565Ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate

Product 1

HCID 140675775-Methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.9 g of sodium hydroxide in 50 ml of water was added to a suspension of 1.66 g of ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate in 30 ml of hot ethanol and the mixture was warmed on a water bath for one hour after which thin layer chromatography showed no ester present. The resulting solution was filtered hot and the filtrate was acidified to a pH of 1-2 with concentrated hydrochloric acid. The mixture was cooled and filtered and the recovered product was rinsed with water and dried over P2O5 under vacuum to obtain 1.40 g (95% yield) of 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylic acid melting at 330°-333° C.

Workup

  1. temperaturethe mixture was warmed on a water bath for one hour after which thin layer chromatography
  2. filtrationThe resulting solution was filtered hot
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe recovered product was rinsed with water
  6. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-5c9f561fc25d4670834c2e2a4de290cd
Source dataset
uspto-grants-1979_04
Patent number
US04151280

Reaction notes

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