N-(4-Bromopentyl)phthalimide → 6-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(9-phenylnonoxy) quinoline

HRID 1030192Notes

Reaction equation

HRID 1030192 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:29][CH3:30])[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].Br[CH:32]([CH3:47])[CH2:33][CH2:34][CH2:35][N:36]1[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]2[C:37]1=[O:46]>CCN(CC)CC>[CH3:30][O:29][C:4]1[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]2[C:11](=[C:2]([NH:1][CH:32]([CH3:47])[CH2:33][CH2:34][CH2:35][N:36]3[C:40](=[O:41])[C:39]4=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]4[C:37]3=[O:46])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

5

Reactant 2

HCID 240534N-(4-Bromopentyl)phthalimide3×HCID 541929178-Amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline

Product 1

HCID 541049706-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(9-phenylnonoxy) quinolineYield 72.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalyst2×HCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 8-amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline (0.85 g, 0.002 mol) and 4-bromo-1-phthalimidopentane (BPP) (2.4 g, 0.008 mol) was heated at 125°-135° C. while Et3N (1 ml) was added in small portions during 0.5 hr. After 2 h, second portions of BPP (0.6 g) and Et3N (2 drops) were introduced. Identical additions of BPP (0.6 g) and Et3N (2 drops) were made three more times at 1 h intervals. The mixture was allowed to cool, extracted with Et2O and the extract was treated with Darco and evaporated to dryness. The residue was redissolved in Et2O (100 ml) and treated with an excess of ethereal hydrogen chloride. The resulting dark red precipitate was separated by decantation, basified with ethereal Et3N and the solvent was evaporated. The residual brown oil was dissolved in CHCl3, placed on a silica gel column (100 g) and eluted with CHCl3. Concentration of the eluate provided 0.9 g (72%) of 6-methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(9-phenylnonoxy) quinoline as a pale brown oil which was used without further purification.

Workup

  1. additionwas added in small portions during 0.5 hr
  2. customat 1 h
  3. temperatureto cool
  4. extractionextracted with Et2O
  5. additionthe extract was treated with Darco
  6. customevaporated to dryness
  7. dissolutionThe residue was redissolved in Et2O (100 ml)
  8. additiontreated with an excess of ethereal hydrogen chloride
  9. customThe resulting dark red precipitate was separated by decantation
  10. customthe solvent was evaporated
  11. dissolutionThe residual brown oil was dissolved in CHCl3
  12. washeluted with CHCl3

Sources & evidence

ORD record
ord-9d6895916b11413f89f454fdec85d3a3
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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