1-Chloro-2,6-dinitrobenzene → 4-(2,6-Dinitrobenzylidene)-1-ethyl-1,4-dihydroquinoline

HRID 1287183Notes

Reaction equation

HRID 1287183 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[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[N+:25]([O-:27])=[O:26].C(N(C(C)C)CC)(C)C>C(#N)C>[N+:22]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:25]([O-:27])=[O:26])[C:16]=1[CH:8]=[C:7]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH2:2][CH3:3])[CH:5]=[CH:6]1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 69062Quinolinium, 1-ethyl-4-methyl-, iodide (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 540122044-(2,6-Dinitrobenzylidene)-1-ethyl-1,4-dihydroquinolineYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethyllepidinium iodide (3.0 g., 10 mmole) and 1-chloro-2,6-dinitrobenzene (2.5 g., 12 mmole) are warmed in acetonitrile (50 ml.) and diisopropylethylamine (2.6 g., 20 mmole) is added. The resulting dark mixture is allowed to cool and stand overnight. The precipitate of dye is filtered off and washed with acetonitrile and ether. On recrystallization from acetonitrile, a 25% yield (0.85 g.) of purified dye is obtained with a m.p. of 154°-155° C. dec.

Workup

  1. temperatureto cool
  2. filtrationThe precipitate of dye is filtered off
  3. washwashed with acetonitrile and ether
  4. customOn recrystallization from acetonitrile
  5. customa 25% yield (0.85 g.) of purified dye is obtained with a m.p. of 154°-155° C. dec.

Sources & evidence

ORD record
ord-33af87ddf59c451298e3aab5131f534e
Source dataset
uspto-grants-1976_10
Patent number
US03984248

Reaction notes

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