Triethylamine → 5-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline

HRID 1583811Notes

Reaction equation

HRID 1583811 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:23][CH3:24])[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:26]([CH3:41])[CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:13]([O:12][C:5]1[C:4]([O:23][CH3:24])=[CH:3][C:2]([NH:1][CH:26]([CH3:41])[CH2:27][CH2:28][CH2:29][N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 240534N-(4-Bromopentyl)phthalimide2×HCID 135359528-Amino-5-decoxy-6-methoxyquinoline

Product 1

HCID 539727355-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinolineYield 49.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 3.65 g of 8-amino-5-decoxy-6-methoxyquinoline and 3.5 g of 4-bromo-1-phthalimidopentane was maintained at 140°-145° while 1 g of triethylamine was added in portions during 1.5 hr. Five more increments of 4-bromo-1-phthalimidopentane (3 g) and triethylamine (1 g) were added at 1.5 hr intervals in the usual manner. The mixture was allowed to cool and extracted with diethyl ether (ca. 300 ml). Treatment of the extract with diethyl ether-hydrochloric acid gave a red oil. The oil was dissolved in chloroform (200 ml) washed with dilute sodium hydroxide (2×30 ml) and water, dried (potassium carbonate) passed through a silica column and concentrated to give 3 g of phthalimide derivative as a red oil. This material was used without further purification.

Workup

  1. additionwas added in portions during 1.5 hr
  2. temperatureto cool
  3. extractionextracted with diethyl ether (ca. 300 ml)
  4. extractionTreatment of the extract with diethyl ether-hydrochloric acid
  5. customgave a red oil
  6. washwashed with dilute sodium hydroxide (2×30 ml) and water
  7. dry with materialdried (potassium carbonate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a79ff084e0784be6a2b91e31289dc598
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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