4-[(7-Chloroquinolin-4-yl)amino]benzoic acid → 4-(7-Chloro-4-quinolylamino)-N-(2-diethylaminoethyl)-N-ethyl-benzamide

HRID 918396Notes

Reaction equation

HRID 918396 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.ClC1[CH:33]=[C:32]2C(C(NC3C=CC(C(O)=O)=CC=3)=[CH:29][CH:30]=[N:31]2)=CC=1>>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([N:10]([CH2:11][CH2:6][N:31]([CH2:30][CH3:29])[CH2:32][CH3:33])[CH2:9][CH3:8])=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 6862834-[(7-Chloroquinolin-4-yl)amino]benzoic acidHCID 215209934-(7-Chloro-4-quinolylamino)benzoyl chloride hydrochloride

Product 1

HCID 215209964-(7-Chloro-4-quinolylamino)-N-(2-diethylaminoethyl)-N-ethyl-benzamide

Procedure

4-(7-Chloro-4-quinolylamino) benzoyl chloride hydrochloride (prepared by refluxing 9.0 grams of 4-(7-chloro-4-quinolylamino) benzoic acid and evaporating the excess thionyl chloride, was added in portions to a cooled, stirred mixture of 4.32 grams of N,N,N1 -triethylethylene diamine and 32 grams of sodium carbonate in 60 milliliters of chloroform and 70 milliliters of water. After stirring for 2 days at room temperature the reaction mixture was filtered, the chloroform layer separated, dried and evaporated to give an oil. This was triturated with hexane to give a light brown solid, which was triturated with acetone to give 5.3 grams of the title compound as a quarter hydrate.

Workup

  1. customevaporating the excess thionyl chloride
  2. additionwas added in portions to a cooled
  3. additionmixture of 4.32 grams of N,N,N1 -triethylethylene diamine and 32 grams of sodium carbonate in 60 milliliters of chloroform and 70 milliliters of water
  4. stirringAfter stirring for 2 days at room temperature the reaction mixture
  5. filtrationwas filtered
  6. customthe chloroform layer separated
  7. customdried
  8. customevaporated
  9. customto give an oil
  10. customThis was triturated with hexane
  11. customto give a light brown solid, which
  12. customwas triturated with acetone

Sources & evidence

ORD record
ord-f0c788dd16904d2eb25e3df3a71fe819
Source dataset
uspto-grants-1976_07
Patent number
US03971787

Reaction notes

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