Hydrochloric Acid → 1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid

HRID 72732Notes

Reaction equation

HRID 72732 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][C:15]([C:21]([O:23]CC)=[O:22])=[CH:14][CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][C:15]([C:21]([OH:23])=[O:22])=[CH:14][CH:13]=4)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59198821Ethyl 1-cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxyate

Product 1

HCID 591986821-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxyate as synthesized in the above Example 57, 3.33 g, ethanol 14 mL and 1N aqueous sodium hydroxide solution 29.4 mL were mixed, and heated under reflux for an hour in nitrogen atmosphere. The reaction liquid was allowed to cool off, and its pH was adjusted to 7 by addition of diluted hydrochloric acid. The precipitated crystals were recovered by filtration, washed with water and dried by heating under reduced pressure to provide 2.96 g of the title compound.

Workup

  1. additionwere mixed
  2. temperatureheated
  3. temperatureunder reflux for an hour in nitrogen atmosphere
  4. customThe reaction liquid
  5. temperatureto cool off
  6. filtrationThe precipitated crystals were recovered by filtration
  7. washwashed with water
  8. customdried
  9. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-94d42711bfab41448cba029d03ace0c6
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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