Triethylamine → 6-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(6-phenylhexoxy) quinoline

HRID 1111388Notes

Reaction equation

HRID 1111388 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([O:27][CH3:28])[C:6]([O: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:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[CH3:13].I[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>CCOCC>[CH3:28][O:27][C:5]1[C:6]([O: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:7]2[C:12](=[C:3]([NH:2][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:4]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH3:13]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 123682034-Iodo-1-phthalimido-pentane2×HCID 679141208-Amino-6-methoxy-4-methyl-5-(6-phenylhexoxy) quinoline hydrochloride

Product 1

HCID 542200426-Methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5-(6-phenylhexoxy) quinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 8-amino-6-methoxy-4-methyl-5-(6-phenylhexoxy) quinoline hydrochloride (2.7 g, 0.007 mol), and 4-iodo-1-phthalimido-pentane (IPP) (3.0 g, 0.009 mol) was maintained at 100° C. while 1 ml of Et3N was added dropwise. After an additional 3 h of IPP and 1 ml of Et3N were added, heating was continued for 4 h and the mixture was allowed to cool, diluted with Et2O (100 ml), filtered, washed with saturated NaCl and dried (Na2SO4). Solvent removal provided a quantitative yield of 6-methoxy-4-methyl-8-(1-methyl-4-phthalimidobutylamino)-5 -(6-phenylhexoxy) quinoline as a brown syrup which was used without further purification.

Workup

  1. additionwas added dropwise
  2. temperatureheating
  3. temperatureto cool
  4. filtrationfiltered
  5. washwashed with saturated NaCl
  6. dry with materialdried (Na2SO4)
  7. customSolvent removal

Sources & evidence

ORD record
ord-8c2036ae5c6249eeb915275b15f3dac4
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

Loading…