Hydrochloric Acid → 4-(7-Chloro-4-aminoquinolyl)-2-diethylaminomethyl-5,6,7,8-tetrahydro-1-naphthol

HRID 1604957Notes

Reaction equation

HRID 1604957 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:16]=[C:15]([NH:17][C:18]([CH3:20])=O)[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:8]=1[OH:21])[CH2:4][CH3:5])[CH3:2].[ClH:22]>C(O)C>[Cl:22][C:8]1[CH:7]=[C:6]2[C:20]([C:18]([NH:17][C:15]3[C:14]4[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=4[C:8]([OH:21])=[C:7]([CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:16]=3)=[CH:2][CH:1]=[N:3]2)=[CH:14][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13801505HCID 13801505, compound

Product 1

HCID 138015064-(7-Chloro-4-aminoquinolyl)-2-diethylaminomethyl-5,6,7,8-tetrahydro-1-naphtholYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2 g of 2-diethylaminomethyl-4-acetamino-5,6,7,8-tetrahydro-I-naphthol, and 50 ml of concentrated hydrochloric acid in 200 ml of absolute ethanol was refluxed for 12 hours. Thereafter the solvent was distilled and the residue treated with ammonium hydroxide then extracted with ether. The etherial extract was washed with water and dried over magnesium sulphate. Then the ether was distilled to reside the amine. From this residual amine 6 g was mixed with 4 g of 4,7-dihchloroquinoline and few drops of conc. HCl in 50 ml of absolute ethanol and refluxed for 12 hours. Thereafter, the reaction mixture was cooled and diluted with water to double its volume then poured over a cold solution of ammonia. The formed precipitate was collected and washed with water. After drying, it weighed 9.2 g (90 % yield) of 4-(7-chloro-4-quinolylamino)-2-diethylaminomethyl-5,6,7,8-tetrahydro-I-naphthol (III). After recrystallization, it melted at 215°-217°C.

Workup

  1. distillationThereafter the solvent was distilled
  2. additionthe residue treated with ammonium hydroxide
  3. extractionthen extracted with ether
  4. extractionThe etherial extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulphate
  7. distillationThen the ether was distilled
  8. additionFrom this residual amine 6 g was mixed with 4 g of 4,7-dihchloroquinoline and few drops of conc. HCl in 50 ml of absolute ethanol
  9. temperaturerefluxed for 12 hours
  10. temperatureThereafter, the reaction mixture was cooled
  11. additiondiluted with water
  12. additionthen poured over a cold solution of ammonia
  13. customThe formed precipitate was collected
  14. washwashed with water
  15. customAfter drying

Sources & evidence

ORD record
ord-f884dd51469f44a88e48fe40a8a8faf5
Source dataset
uspto-grants-1976_04
Patent number
US03948920

Reaction notes

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