Triethylamine → 6-Methoxy-8-(1-methyl-4-phthalimidobutylamino)-4-(3-trifluoromethylstyryl)quinoline

HRID 1863102Notes

Reaction equation

HRID 1863102 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1.Br[CH:27]([CH3:42])[CH2:28][CH2:29][CH2:30][N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:25][O:24][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([NH:1][CH:27]([CH3:42])[CH2:28][CH2:29][CH2:30][N:31]3[C:35](=[O:36])[C:34]4=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]4[C:32]3=[O:41])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 240534N-(4-Bromopentyl)phthalimideHCID 6313208-Amino-6-methoxy-4-(3-trifluoromethylstyryl)quinoline

Product 1

HCID 6329016-Methoxy-8-(1-methyl-4-phthalimidobutylamino)-4-(3-trifluoromethylstyryl)quinolineYield 78.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 8.4 g (0.025 mole) of 8-amino-6-methoxy-4-(3-trifluoromethylstyryl)quinoline, 7.3 g (0.025 mole) of 4-bromo-1-phthalimidopentane and 2.5 g of triethylamine was heated in an oil bath at 130°-135° for 12 hr. The reaction mixture ws dissolved in chloroform and passed through a silica gel column to give 11 g of crude product which was used without further purification. Crystallization from ethanol provided an analytical sample as yellow needles, mp 154°-156°.

Workup

  1. temperaturewas heated in an oil bath at 130°-135° for 12 hr

Sources & evidence

ORD record
ord-e390b6d44cb54ab3b2826f1612d776c9
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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