Water → 8-Quinolinecarboxamide

HRID 236870Notes

Reaction equation

HRID 236870 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C([N:17](CC)CC)C.COC(Cl)=O.O>CC(C)=O.CC1C=CC(CCN)=CC=1>[N:8]1[C:9]2[C:4](=[CH:3][CH:2]=[CH:11][C:10]=2[C:12]([NH2:17])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 1654926-Chloro-8-quinolinecarboxylic acid

Product 1

HCID 1506648-Quinolinecarboxamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 76751p-MethylphenethylamineSolvent2×

Procedure

5.2 g of 6-chloro-quinoline-8-carboxylic acid in 150 ml of acetone were combined, while stirring and cooling with ice, with 2.8 g of triethylamine and 2.6 g of chloroformic acid methyl ester. The whole was stirred for about 10 minutes, a solution of 3.4 g of 2-(4-methylphenyl)-ethylamine in 50 ml of 2-(4-methylphenyl)-ethyl-amine in 50 ml of acetone was added and the mixture was again stirred for 1 hour at room temperature. Then, water was added, the precipitate was filtered off with suction, treated with a dilute ammonia solution, undissolved matter was filtered off and recrystallized from dilute methanol. The 6-chloro-N-(2-<4-methylphenyl>-ethyl)-quinoline-8-carboxylic acid amide so obtained was found to melt at 102°-104° C.

Workup

  1. stirringThe whole was stirred for about 10 minutes
  2. stirringthe mixture was again stirred for 1 hour at room temperature
  3. filtrationthe precipitate was filtered off with suction
  4. additiontreated with a dilute ammonia solution, undissolved matter
  5. filtrationwas filtered off
  6. customrecrystallized from dilute methanol

Sources & evidence

ORD record
ord-b805e0eef3bd43c6aed0b139ab058722
Source dataset
uspto-grants-1979_06
Patent number
US04158063

Reaction notes

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