Quinolinium, 1-ethyl-4-methyl-, iodide (1:1) → 4-(4-Ethoxycarbonyl-2-nitrobenzylidene)-1-ethyl-1,4-dihydroquinoline

HRID 436707Notes

Reaction equation

HRID 436707 reaction equation
[I-].[CH2:2]([N+:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7]([CH3:8])=[CH:6][CH:5]=1)[CH3:3].Cl[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][C:17]=1[N+:27]([O-:29])=[O:28].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:23]([O:22][C:20]([C:19]1[CH:25]=[CH:26][C:16]([CH:8]=[C:7]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:4]([CH2:2][CH3:3])[CH:5]=[CH:6]2)=[C:17]([N+:27]([O-:29])=[O:28])[CH:18]=1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 69062Quinolinium, 1-ethyl-4-methyl-, iodide (1:1)HCID 81531DiisopropylethylamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 544708754-(4-Ethoxycarbonyl-2-nitrobenzylidene)-1-ethyl-1,4-dihydroquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethyllepidinium iodide (5.8 g., 19.4 mmole) and ethyl 4-chloro-3-nitrobenzoate (4.6 g., 20 mmole) are stirred together in acetonitrile (50 ml.). Diisopropylethylamine (5.2 g., 40 mmole) is added and the mixture refluxed on a steam bath for 6 hours. The mixture is dissolved in 500 ml. ether and extracted five times with 200 ml. portions of water. The ether extract is dried over anhydrous magnesium sulfate. The dried ether solution is evaporated to dryness and then taken up on 25 ml. ether and chilled overnight. The precipitated dye is filtered off, washed with ether and petroleum ether, and dried. The yield is 2.8 g. (40%) with a m.p. of about 100° C.

Workup

  1. temperaturethe mixture refluxed on a steam bath for 6 hours
  2. dissolutionThe mixture is dissolved in 500 ml
  3. extractionether and extracted five times with 200 ml
  4. extractionThe ether extract
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. customThe dried ether solution is evaporated to dryness
  7. temperatureether and chilled overnight
  8. filtrationThe precipitated dye is filtered off
  9. washwashed with ether and petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-bbb93e00fc9345b892ddfe6f23af623c
Source dataset
uspto-grants-1977_06
Patent number
US04028113

Reaction notes

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