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

HRID 1111392Notes

Reaction equation

HRID 1111392 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][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(P(N(C)C)(N(C)C)=O)C.C1OC1C>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][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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

6

Reactant 4

HCID 6378Propylene OxideHCID 12679HexamethylphosphoramideHCID 563758(8-Bromooctyl)benzeneHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline2×

Product 1

HCID 543454366-Methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinolineYield 60.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (4.98 g, 0.02 mol), 1-bromo-8-phenyloctane (4.7 g, 0.017 mol) and HMPA (13 ml), at 120° C., was added, dropwise, during 1 h, a mixture of propylene oxide (6 ml) and Et3N (1 ml). The reaction was continued for 3.5 h, allowed to cool and extracted successively with pet ether, Et2O and Me2CO leaving 1 g of insoluble starting material, 5-hydroxy-6-methoxy-4methyl-8-nitroquinoline. The combined pet ether and Et2O extracts were washed (H2O, dil NaOH, H2O), dried (Na2SO4) and concentrated. The residue was dissolved in CHCl3, placed on a silica gel column and eluted with CHCl3. Concentration of the eluates left an oil which was triturated with pet ether to give 4.35 g (60%) of 6-methoxy-4-methyl-8-nitro-5(8-phenyloctoxy) quinoline as yellow solid, mp 39.5°-41° C. Crystallization from hexane (Darco) provided the analytical sample as yellow crystals, mp 41°-42° C.

Workup

  1. additionat 120° C., was added
  2. waitThe reaction was continued for 3.5 h
  3. temperatureto cool
  4. extractionextracted successively with pet ether, Et2O and Me2CO
  5. customleaving 1 g
  6. washThe combined pet ether and Et2O extracts were washed (H2O, dil NaOH, H2O)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in CHCl3
  10. washeluted with CHCl3
  11. waitConcentration of the eluates left an oil which
  12. customwas triturated with pet ether

Sources & evidence

ORD record
ord-584e83ea3cec4498a9df48b9932e3392
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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