Ethanol → HCID 13394076, compound

HRID 1583546Notes

Reaction equation

HRID 1583546 reaction equation
C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:20])=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)(=O)C.O.[CH2:22](O)[CH3:23].C(Br)C>[OH-].[Na+]>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[C:10]([C:15]([OH:17])=[O:16])=[CH:11][N:12]2[CH2:22][CH3:23])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 6332Ethyl BromideHCID 178469623HCID 178469623, compound

Product 1

HCID 13394076HCID 13394076, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4.6 Grams of ethyl 7-acetamido-4-hydroxy-3-quinolinecarboxylate are dissolved in 15 ml of 10% NaOH, 60 ml of H2O and 100 ml of ethanol, and 5 ml of ethyl bromide are added. The mixture is left under reflux for 4 hours, then the excess of ethyl bromide and ethanol is evaporated off, and 10 ml of 10% NaOH are then added. The mixture is heated under reflux for 2 hours, allowed to cool, acidified with HCl, filtered and treated with ethanol at 70° C. The product is filtered off and recrystallized in a dimethylformamide/water (1:1) mixture. 1.0 Gram of a solid is obtained, of melting point 304°-307° C.

Workup

  1. waitThe mixture is left
  2. temperatureunder reflux for 4 hours
  3. customthe excess of ethyl bromide and ethanol is evaporated off
  4. addition10 ml of 10% NaOH are then added
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 2 hours
  7. temperatureto cool
  8. filtrationfiltered
  9. additiontreated with ethanol at 70° C
  10. filtrationThe product is filtered off
  11. customrecrystallized in a dimethylformamide/water (1:1) mixture
  12. custom1.0 Gram of a solid is obtained, of melting point 304°-307° C.

Sources & evidence

ORD record
ord-c954ab24e3934f1eb1e31ee71cb60546
Source dataset
uspto-grants-1985_11
Patent number
US04552882

Reaction notes

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