2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14748413, compound

HRID 1649722Notes

Reaction equation

HRID 1649722 reaction equation
[CH2:1]([CH:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]1C(OC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23]C1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH2:1]([C:8]1[CH:13]=[C:12]([Cl:23])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19854561HCID 19854561, compound

Product 1

HCID 14748413HCID 14748413, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The crude dihydropyridine intermediate is dissolved in benzene (100 ml) and heated to 65°. A solution of 2,3-dichloro 5,6-dicyanobenzoquinone (5.0 q) in warm benzene (50 ml) is added dropwise with stirring. The reaction mixture is stirred at 65° for one hour and then cooled to room temperature. The mixture is washed with 10% aqueous sodium bicarbonate (two portions of 100 ml each) and water (100 ml), then extracted with 2N hydrochloric acid (two portions of 150 ml each). The combined acid extracts are made alkaline with dilute aqueous sodium hydroxide and extracted with diethyl ether. After drying and concentration, the title compound is obtained as an oil (0.95 g) that can be further purified by chromatography on silica gel (using 4:1 by volume hexane-ethyl acetate as eluent). Structure assignment is confirmed by nmr spectroscopy. nmr (CDCl3): δ (ppm) 4.16 (s, 2H); 7.14-7.40 (m, 7H); 8.46 (d, 1H).

Workup

  1. temperatureheated to 65°
  2. stirringThe reaction mixture is stirred at 65° for one hour
  3. washThe mixture is washed with 10% aqueous sodium bicarbonate (two portions of 100 ml each) and water (100 ml)
  4. extractionextracted with 2N hydrochloric acid (two portions of 150 ml each)
  5. extractionextracted with diethyl ether
  6. customAfter drying
  7. concentrationconcentration

Sources & evidence

ORD record
ord-d381751bc99942bf8751c21866ad10cc
Source dataset
uspto-grants-1990_05
Patent number
US04921857

Reaction notes

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