Sodium Carbonate → 1-Chloro-6-methoxy-7-methylisoquinoline

HRID 1366752Notes

Reaction equation

HRID 1366752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=O)[NH:8][CH:7]=[CH:6]2.P(Cl)(Cl)([Cl:17])=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:17][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH3:13])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 181763916-Methoxy-7-methylisoquinolin-1(2H)-one

Product 1

HCID 537828801-Chloro-6-methoxy-7-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of 6-methoxy-7-methyl-2H-isoquinolin-1-one (5 g, 26.45 mmol) was treated at room temperature with phosphorus oxychloride (22 ml). The mixture was heated at 100° C. for 1 h with stirring then concentrated in vacuo to give a residue. Toluene was added to the residue which was further concentrated in-vacuo to give a residue which was taken up in toluene and slowly added to saturated aqueous sodium carbonate. The toluene layer was then separated. The aqueous layer was further mixed and extracted with toluene. The combined toluene layers were dried (MgSO4) and concentrated in vacuo to give a residue. The residue was triturated with diethyl ether then filtered and dried in vacuo to give 1-chloro-6-methoxy-7-methyl-isoquinoline (4 g, 19.32 mmol).

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give a residue
  3. customto give a residue which
  4. customThe toluene layer was then separated
  5. additionThe aqueous layer was further mixed
  6. extractionextracted with toluene
  7. dry with materialThe combined toluene layers were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue was triturated with diethyl ether
  11. filtrationthen filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-04526d70d18d4bf1bd7df4fc422e2daf
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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