Triethylamine → 5-Dimethylamino-6-methoxy-8-[1-methyl-4-phthalimidobutylamino]quinoline

HRID 1863111Notes

Reaction equation

HRID 1863111 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([N:12]([CH3:14])[CH3:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:18]([CH3:33])[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C(N(CC)CC)C>CC(C)=O>[CH3:14][N:12]([CH3:13])[C:5]1[C:4]([O:15][CH3:16])=[CH:3][C:2]([NH:1][CH:18]([CH3:33])[CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 240534N-(4-Bromopentyl)phthalimide2×HCID 6124918-Amino-5-dimethylamino-6-methoxyquinoline

Product 1

HCID 6185705-Dimethylamino-6-methoxy-8-[1-methyl-4-phthalimidobutylamino]quinoline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 17.2 g (0.033 mole) of 8-amino-5-dimethylamino-6-methoxyquinoline and 9.8 g (0.033 mole) of 4-bromo-1-phthalimidopentane was maintained at 145° while 5 ml of triethylamine was added dropwise. Addition of 9.8 g of 4-bromo-1-phthalimidopentane and 5 ml of triethylamine was repeated three more times, at the same temperature (145°) at 2 hr intervals. The mixture was allowed to cool, diluted with acetone and filtered. The filtrate was concentrated to a brown oil which was diluted with ether, washed with 30% KOH and extracted with chloroform. The extract was passed through a silica column and the eluate was concentrated, dissolved in ether, treated with Darco and slowly evaporated to give yellow crystals which, after washing with petroleum ether (bp 20°-40°) weighed 9.5 g and melted at 103°-105°.

Workup

  1. additionwas added dropwise
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to a brown oil which
  5. additionwas diluted with ether
  6. washwashed with 30% KOH
  7. extractionextracted with chloroform
  8. concentrationthe eluate was concentrated
  9. dissolutiondissolved in ether
  10. additiontreated with Darco
  11. customslowly evaporated
  12. customto give yellow crystals which
  13. washafter washing with petroleum ether (bp 20°-40°)

Sources & evidence

ORD record
ord-306f25fcc1e64e8e975b98d6bbc7d09b
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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