Lithium Chloride → HCID 24962934, compound

HRID 1522830Notes

Reaction equation

HRID 1522830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13]C)[CH:12]=1)[C:9](=[O:15])[N:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:7]=[CH:6]2.[Li+].[Cl-]>>[OH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[C:9](=[O:15])[N:8]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 433294Lithium ChlorideHCID 57557415HCID 57557415, compound

Product 1

HCID 24962934HCID 24962934, compoundYield 83.7%

Conditions

Temperature
140 °C

Procedure

6,8-Dimethoxy-2-(4-methoxyphenyl)isoquinolin-1(2H)-one (2.25 g, 7.23 mmol) and LiCl (6.12 g, 144.54 mmol) were placed in a dry, argon flushed 150 mL three-necked flask fitted with a stirring bar and reflux condenser. Anhydrous DMF (30 mL) was added via a syringe. The reaction mixture was heated to 140° C. under vacuum for 20 h. Then, the reaction was quenched by addition of 30 mL of 2N HCl solution. The solution was extracted with EtOAc (3×30 mL). The extracts were combined and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica-gel, EtOAc) to give a white solid product, 1.80 g, 83.7% yield. 1H NMR (DMSO-d6, 300 MHz): δ 12.98 (s, 1H), 7.42-7.35 (m, 3H), 7.06 (d, 2H, J=9.0 Hz), 6.70-6.67 (m, 2H), 6.45 (d, 1H, J=2.1 Hz), 3.85 (s, 3H), 3.82 (s, 3H).

Workup

  1. customflushed 150 mL three-necked flask
  2. customfitted with a stirring bar
  3. temperaturereflux condenser
  4. additionAnhydrous DMF (30 mL) was added via a syringe
  5. customThen, the reaction was quenched by addition of 30 mL of 2N HCl solution
  6. extractionThe solution was extracted with EtOAc (3×30 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica-gel, EtOAc)
  10. customto give a white solid product, 1.80 g, 83.7% yield

Sources & evidence

ORD record
ord-3901b3fb894346c0a888aab4fe4f6b9c
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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