HCID 178469488, compound → HCID 178524702, compound

HRID 1657448Notes

Reaction equation

HRID 1657448 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:10]=2)([O:3]CC)=[O:2]>C(O)C.[OH-].[Na+]>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:1]([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 178469488HCID 178469488, compound

Product 1

HCID 178524702HCID 178524702, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 15 g of 3-carboethoxy-4-hydroxy-7-cyclohexyl-quinoline in 150 ml of ethanol and 150 ml of 2 N sodium hydroxide solution is boiled under reflux for 7 hours. It is then evaporated to dryness, the residue is dissolved in ethanol-water and the solution is adjusted to pH value 7 with 2 N hydrochloric acid. The crystalline residue thereby produced is filtered off and thoroughly washed with water. 4-Hydroxy-7-cyclohexylquinoline-3-carboxylic acid thus obtained, melts at 241°-243°C (evolution of gas).

Workup

  1. temperatureunder reflux for 7 hours
  2. customIt is then evaporated to dryness
  3. dissolutionthe residue is dissolved in ethanol-water
  4. customThe crystalline residue thereby produced
  5. filtrationis filtered off
  6. washthoroughly washed with water

Sources & evidence

ORD record
ord-9696c01a04bf4f6292e00c4e3c4a1658
Source dataset
uspto-grants-1976_06
Patent number
US03960868

Reaction notes

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