Propylene Oxide → 6-Methoxy-4-methyl-8-nitro-5-(6-phenylhexoxy) quinoline

HRID 1111387Notes

Reaction equation

HRID 1111387 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[C:4]([CH3:17])=[CH:5][CH:6]=[N:7]2.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(P(N(C)C)(N(C)C)=O)C.C1OC1C>C(Cl)(Cl)Cl.CCN(CC)CC>[CH3:13][O:12][C:11]1[C:2]([O:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:3]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=1)[N:7]=[CH:6][CH:5]=[C:4]2[CH3:17]

Participants

7

Reactant 4

HCID 6378Propylene Oxide3×HCID 12679HexamethylphosphoramideHCID 561788(6-Bromohexyl)benzene2×HCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

Product 1

HCID 545638326-Methoxy-4-methyl-8-nitro-5-(6-phenylhexoxy) quinolineYield 58.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent3×

Procedure

To a stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (2.3 g, 0.01 mole), 1-bromo-6-phenylhexane (2.4 g, 0.01 mole) and HMPA (25 ml), at 130° C., was added dropwise, during 2 h, a mixture of Et3N (1ml) and propylene oxide (9 ml). After four more hours, an additional 10 ml of the Et3N--propylene oxide mixture was introduced. Heating was continued for 24 h and 1.2 g (0.005 mole) of 1-bromo-6-phenylhexane was added followed by another 10 ml of Et3N--propylene oxide. This final mixture was heated for 6 h, allowed to cool, diluted with CHCl3 (50 ml), placed on a silica gel column and eluted with CHCl3. Concentration of the yellow eluate gave 2.3 g of 6-methoxy-4-methyl-8-nitro-5-(6-phenylhexoxy) quinoline as an oil which was used without further purification.

Workup

  1. additionat 130° C., was added dropwise, during 2 h
  2. temperatureHeating
  3. temperatureto cool
  4. washeluted with CHCl3

Sources & evidence

ORD record
ord-94966d6284b2460ab9bd1b8ea9a54e03
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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