Propylene Oxide → 6-Methoxy-4-methyl-8-nitro-5-[4-phenylbutoxy]quinoline

HRID 1111389Notes

Reaction equation

HRID 1111389 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][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1OC1C.COC1C(OCCCCCCCC2C=CC=CC=2)=C2C(=C([N+]([O-])=O)C=1)N=CC=C2C>CCOCC.CCN(CC)CC.CN(P(N(C)C)(N(C)C)=O)C>[CH3:13][O:12][C:11]1[C:2]([O:1][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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

8

Reactant 4

HCID 6378Propylene OxideHCID 2596681-Bromo-4-phenylbutaneHCID 6163856-Methoxy-4-methyl-8-nitro-5-(7-phenylheptoxy)quinolineHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline2×

Product 1

HCID 5635176-Methoxy-4-methyl-8-nitro-5-[4-phenylbutoxy]quinoline

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred mixture of 5-hydroxy-6methoxy-4-methyl-8-nitroquinoline (5.9 g, 0.025 mol), 1-bromo-4-phenylbutane (4.3 g, 0.02 mol) and HMPA (15 ml), at 110°-115° C., was added dropwise, during 1 h, a mixture of propylene oxide (6 ml) and Et3N (1 ml). The reaction was continued for 5 h, allowed to cool and extracted successively with pet ether, Et2O and Me2CO leaving 1.1 g of insoluble starting material, 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline. The pet ether and Et2O fractions were worked up as described above for 6-methoxy-4-methyl-8-nitro-5-(7-phenylheptoxy)quinoline (see example 1, part b) to give crude 6-methoxy-4-methyl-8-nitro-5(4-phenylbutoxy) quinoline as an oil. This material was dissolved in CHCl3, placed on a silica gel column and eluted with CHCl3. The eluates were concentrated to an oil which on trituration with pet ether gave 3.2 g (43%) of 6-methoxy-4-methyl-8-nitro-5-(4-phenylbutoxy) quinoline as yellow-green crystals, mp 88°-89° C. Recrystallization from hexane provided the analytical sample, mp 90°-91° C.

Workup

  1. additionat 110°-115° C., was added dropwise, during 1 h
  2. temperatureto cool
  3. extractionextracted successively with pet ether, Et2O and Me2CO
  4. customleaving 1.1 g

Sources & evidence

ORD record
ord-42d907213b4a4b04997a8e6b5e3477ce
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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