Water → HCID 178457722, compound

HRID 544407Notes

Reaction equation

HRID 544407 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[H-].[Na+].O>C(N)CC>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([NH:5][CH2:4][CH2:3][CH3:2])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178469510HCID 178469510, compound

Product 1

HCID 178457722HCID 178457722, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2.17 g of ethyl 4-hydroxy-3-quinoline-carboxylate in 20 ml of propylamine in the presence of traces of sodium hydride was refluxed and then was stirred at 50° C. for 16 hours. The mixture was pouredinto water and the suspension was vacuum filtered. The product was washed with water, dried in an oven at 100° C. and was crystallized from methanol to obtain 1.1 g of 4-hydroxy-N-propyl-3-quinoline-carboxamide melting at 210° C.

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. washThe product was washed with water
  4. customdried in an oven at 100° C.
  5. customwas crystallized from methanol

Sources & evidence

ORD record
ord-766d605a06974d728d5238eb5ea527d5
Source dataset
uspto-grants-1984_05
Patent number
US04450167

Reaction notes

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