Hydrochloric Acid → HCID 21840843, compound

HRID 1739441Notes

Reaction equation

HRID 1739441 reaction equation
B(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[NH2:10].[C:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)#N.Cl.[OH-:25].[Na+]>ClCCCl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:11]([C:16](=[O:25])[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][C:13]=1[O:14][CH3:15])[NH2:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 75064-CyanopyridineHCID 14798Sodium HydroxideHCID 227703,4-DimethoxyanilineHCID 25135Boron Trichloride

Product 1

HCID 21840843HCID 21840843, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To 1,2-dichloroethane (150 ml) is added boron chloride (25 g) under ice-cooling, and the mixture is stirred for 15 minutes. To the reaction mixture is added dropwise a solution of 3,4-dimethoxyaniline (36.3 g) in 1,2-dichloroethane (150 ml), and thereto is added 4-cyanopyridine (27.1 g). The reaction mixture is heated under reflux overnight, and thereto is added 2 M hydrochloric acid (160 ml). The mixture is heated with stirring at 80° C. for two hours, and thereto is added a 2 M aqueous sodium hydroxide solution (450 ml) under ice-cooling. The mixture is separated to collect the 1,2-dichloroethane layer, and the aqueous layer is extracted with ethyl acetate. The organic layers are combined, washed, dried and concentrated. The residue is crystallized from ether to give 3,4-dimethoxy-6-isonicotinoylaniline (13.1 g).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux overnight
  4. temperatureThe mixture is heated
  5. stirringwith stirring at 80° C. for two hours
  6. temperaturecooling
  7. customThe mixture is separated
  8. customto collect the 1,2-dichloroethane layer
  9. extractionthe aqueous layer is extracted with ethyl acetate
  10. washwashed
  11. customdried
  12. concentrationconcentrated
  13. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-5452dcbe425c4672a4aad9fe32b78d36
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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