Hydrochloric Acid → HCID 21840827, compound

HRID 1739421Notes

Reaction equation

HRID 1739421 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:7]([C:12](=O)[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[C:21]([O:27][CH3:28])(=[O:26])[CH2:22][C:23]([CH3:25])=O.Cl.C(=O)([O-])O.[Na+]>C(O)(=O)C>[Cl:19][C:15]1[CH:14]=[C:13]([C:12]2[C:7]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:9]([O:10][CH3:11])[CH:8]=3)[N:6]=[C:23]([CH3:25])[C:22]=2[C:21]([O:27][CH3:28])=[O:26])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 516892Sodium BicarbonateHCID 21840838HCID 21840838, compound

Product 1

HCID 21840827HCID 21840827, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4-dimethoxy-6-(2-chloroisonicotinoyl)aniline (2.93 g), methyl acetoacetate (2.16 ml), conc. hydrochloric acid (0.1 ml) and acetic acid (30 ml) is heated under reflux for two hours. The reaction mixture is cooled to room temperature, and thereto is added an aqueous sodium hydrogen carbonate solution. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and concentrated. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=9:1) to give 2-chloro-4-(6,7-dimethoxy-3-methoxycarbonyl-2-methylquinolin-4-yl)pyridine (3.0 g).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for two hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-15c4253bdd2c42aa965f2a60626af1c7
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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