Acetic Acid → HCID 21840849, compound

HRID 1739416Notes

Reaction equation

HRID 1739416 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-].[H-].[Na+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:17]([C:22](=O)[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:18][C:19]=1[O:20][CH3:21])[CH:15]=O.C(O)(=O)C>CN(C)C=O>[Cl:29][C:25]1[CH:24]=[C:23]([C:22]2[C:17]3[C:14](=[CH:13][C:12]([O:11][CH3:10])=[C:19]([O:20][CH3:21])[CH:18]=3)[CH:15]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:1]=2)[CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 547815Methyl isocyanoacetateHCID 21840832HCID 21840832, compound

Product 1

HCID 21840849HCID 21840849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl isocyanoacetate (18 ml) in dimethylformamide (85 ml) is added sodium hydride (7.85 g, 62.4% in oil) with ice-cooling under nitrogen atmosphere, and the mixture is stirred at room temperature for 30 minutes. To a solution of 3,4-dimethoxy-6-(2-chloroisonicotinoyl)benzaldehyde (52.0 g) in dimethylformamide (170 ml) is added dropwise the above solution at 40-50° C., and then the mixture is stirred at 50° C. for one hour. The mixture is neutralized with 10% acetic acid, concentrated, and extracted with chloroform. The extract is washed, and the insoluble materials are collected by filtration, and the filtrate is dried and concentrated. The resultant and the collected insoluble materials are combined, and recrystallized from ether-methanol to give 2-chloro-4-(3-methoxycarbonyl-6,7-dimethoxyisoquinolin-1-yl)pyridine (16.1 g).

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. stirringthe mixture is stirred at 50° C. for one hour
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. washThe extract is washed
  6. filtrationthe insoluble materials are collected by filtration
  7. customthe filtrate is dried
  8. concentrationconcentrated
  9. customrecrystallized from ether-methanol

Sources & evidence

ORD record
ord-830afd49704445afb6e7327b761b4bf2
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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