Acetic Anhydride → 2-[3-(2-Cyano-4-nitrophenyl)allylidene]-1-ethyl-1,2-dihydroquinoline

HRID 371902Notes

Reaction equation

HRID 371902 reaction equation
[I-].N([CH:9]=[CH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]=1[CH2:21][CH3:22])C1C=CC=CC=1.[C:23]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[CH3:34])#[N:24].C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C)C=O>[C:23]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[CH:34]=[CH:9][CH:10]=[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH2:21][CH3:22])#[N:24]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3501432-Methyl-5-nitrobenzonitrileHCID 706240322-(2-Anilinoethenyl)-1-ethylquinolin-1-ium iodide

Product 1

HCID 536695452-[3-(2-Cyano-4-nitrophenyl)allylidene]-1-ethyl-1,2-dihydroquinolineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The condensation of 4.02 g. (0.01 mole) of 2-(2-anilinovinyl)-1-ethylquinolinium iodide (prepared as described in British Pat. No. 344,409 m.p. 263°-5° C (dec.)) with 2-cyano-4-nitrotoluene (1.67 g., 0.01 mole) was effected in 15 ml. of dimethylformamide containing 2 ml. of acetic anhydride by heating the reaction mixture to reflux, adding 1.01 g. (0.01 mole) of triethylamine, heating at reflux for 1 to 2 minutes and cooling rapidly. The precipitate was collected, washed successively with dimethylformamide, water and ether and then dried to yield 47% of theory of blue dye base m.p. 250°-252° C.

Workup

  1. customThe condensation of 4.02 g
  2. temperatureto reflux
  3. additionadding 1.01 g
  4. temperatureat reflux for 1 to 2 minutes
  5. temperaturecooling rapidly
  6. customThe precipitate was collected
  7. washwashed successively with dimethylformamide, water and ether
  8. customdried

Sources & evidence

ORD record
ord-2c5da17b135d48e981516ecfbf3ee83b
Source dataset
uspto-grants-1978_05
Patent number
US04088497

Reaction notes

Loading…