N-(4-Bromopentyl)phthalimide → 6-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(7-phenylheptoxy) quinoline

HRID 1111385Notes

Reaction equation

HRID 1111385 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:27][CH3:28])[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].Br[CH:30]([CH3:45])[CH2:31][CH2:32][CH2:33][N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44]>CCN(CC)CC>[CH3:28][O:27][C:4]1[C:5]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]2[C:11](=[C:2]([NH:1][CH:30]([CH3:45])[CH2:31][CH2:32][CH2:33][N:34]3[C:38](=[O:39])[C:37]4=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]4[C:35]3=[O:44])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

4

Reactant 2

HCID 240534N-(4-Bromopentyl)phthalimide3×HCID 6091518-Amino-6-methoxy-4-methyl-5-[7-phenylheptoxy]quinoline

Product 1

HCID 539807316-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(7-phenylheptoxy) quinolineYield 76.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent3×

Procedure

A stirred mixture of 8-amino-6-methoxy-4-methyl-5-(7-phenylheptoxy) quinoline [Example 1c] (9.2 g, 0.024 mol) and 4-bromo-1-phthalimidopentane (BPP) (15 g, 0.05 mol) was heated at 120°-125° C. while Et3N (5 ml) was added in small portions. After 3 h at 120°-125° C., second portions of BPP (7.5g) and Et3N (2.5 ml) were added and heating was continued for 4 h. Third portions of BPP (3 g) and Et3N (1 ml) were introduced, and heating was continued for 2 h. The reaction was allowed to cool and extracted with Et2O (total, ca. 500 ml). The extract was treated with carbon and then with saturated ethereal hydrogen chloride (300 ml). The resulting dark red semi-solid mass was separated and basified with Et2O - Et3N. Concentration of the ethereal solution left 11.5 g (81%) of brown oil which was dissolved in CHCl3, placed on a silica gel column (200 g) and eluted with CHCl3. The first six eluates (75 ml each) were combined and concentrated to give 10.9 grams of 6-methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(7-phenylheptoxy) quinoline which was used without further purification.

Workup

  1. additionwas added in small portions
  2. temperatureheating
  3. waitwas continued for 4 h
  4. temperatureheating
  5. waitwas continued for 2 h
  6. temperatureto cool
  7. extractionextracted with Et2O (total, ca. 500 ml)
  8. additionThe extract was treated with carbon
  9. customThe resulting dark red semi-solid mass was separated
  10. waitConcentration of the ethereal solution left 11.5 g (81%) of brown oil which
  11. dissolutionwas dissolved in CHCl3
  12. washeluted with CHCl3
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-461c3ccc6a5d473085bad1354d7d69d0
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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