Ethanol → HCID 14501165, compound

HRID 2107315Notes

Reaction equation

HRID 2107315 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]([C:17](N)=[O:18])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:21].[CH2:25](O)[CH3:26]>>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]([C:17]([O:18][CH2:25][CH3:26])=[O:21])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14501164HCID 14501164, compound

Product 1

HCID 14501165HCID 14501165, compoundYield 85%

Procedure

To 0.17 g of 5-morpholino-8-quinolinecarboxamide (Compound No. 22) 10 ml of anhydrous ethanol and 2 ml of concentrated sulfuric acid were added, and the mixture was heated under reflux. The solvent was evaporated and the residue was neutralized with saturated aqueous solution of sodium bicarbonate. After extraction with ethyl acetate, the extract was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated, and the residue was refined by column chromatography on silica gel using chloroform-n-hexane (3:2) as an eluent. The crystals thus obtained were recrystallized from chloroform-ether to yield 0.16 g (yield: 85%) of ethyl 5-morpholino-8-quinolincarboxylate (Compound No. 23).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customThe solvent was evaporated
  4. extractionAfter extraction with ethyl acetate
  5. washthe extract was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEthyl acetate was evaporated
  8. customThe crystals thus obtained
  9. customwere recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-847d81b17e834c6ba2fd5847eda95e70
Source dataset
uspto-grants-1990_06
Patent number
US04933447

Reaction notes

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