Phosphorus oxychloride → HCID 22503597, compound

HRID 1251258Notes

Reaction equation

HRID 1251258 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([CH3:11])=[CH:7][CH:8]=[CH:9][CH:10]=1)=O.[C:12]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH3:21])[CH:15]=1)#[N:13].P(Cl)(Cl)(Cl)=O.[CH2:27]([N:29]1[CH2:34]CN[CH2:31][CH2:30]1)[CH3:28]>C(Cl)Cl.CO>[CH2:27]([N:29]1[CH2:30][CH2:31][N:2]([C:3]2[C:5]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[N:13]=2)[CH2:1][CH2:34]1)[CH3:28]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 75111N-methyl-2-toluamideHCID 791961-EthylpiperazineHCID 72048872-Methoxyisonicotinonitrile

Product 1

HCID 22503597HCID 22503597, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

To 3-(2-methoxypyridin-4-yl)isoquinolin-1-one (1.22 g) obtained by reacting N-methyl-o-toluamide (2.90 g) and 4-cyano-2-methoxypyridine (2.60 g) according to the method of Example 10-1 was added phosphorus oxychloride (25.7 g), and the resulting mixture was heated at 100° C. for 2 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting 1-chloro-3-(2-methoxyphenyl)isoquinoline was reacted as it was with N-ethylpiperazine (20 ml) at 120° C. for 8 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to the free compound of the title compound as a pale yellow oil (0.62 g, yield; 9.2%).

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate
  3. custompurified water
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting 1-chloro-3-(2-methoxyphenyl)isoquinoline was reacted as it
  8. customThe reaction solution was evaporated
  9. additionto the resulting residue were added ethyl acetate
  10. custompurified water
  11. washThe ethyl acetate layer was washed with water and brine
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-10608509232e4a7880f64ddc978b741a
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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