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

HRID 1288398Notes

Reaction equation

HRID 1288398 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 aligned to cool and stand overnight. The precipitate of dye is filtered off and washed with acetonitrile and ether. On recrystallization from acetonitrile, 25% yield (0.85 g.) of purified dye is obtained with a m.p. of 45°-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, 25% yield (0.85 g.) of purified dye
  5. customis obtained with a m.p. of 45°-155° C. dec.

Sources & evidence

ORD record
ord-07826b87f0cf495abdce9ba489349bf7
Source dataset
uspto-grants-1976_10
Patent number
US03988156

Reaction notes

Loading…