Phosphorus oxychloride → HCID 86683278, compound

HRID 2361604Notes

Reaction equation

HRID 2361604 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:13][CH3:14])=[CH:7][NH:8][C:9]2=O)=[CH:4][C:3]=1[O:15][CH3:16].O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:15][CH3:16])=[C:2]([F:1])[CH:11]=2)[C:6]([O:13][CH3:14])=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70978615HCID 70978615, compound

Product 1

HCID 86683278HCID 86683278, compoundYield 24.3%

Procedure

A solution of 7-fluoro-4,6-dimethoxyisoquinolin-1(2H)-one (7.6 g, 34.1 mmol) in POCl3 (50 ml) was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (2 g, 24.3%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.88-7.85 (d, J=12 Hz, 1H), 7.75 (s, 1H), 7.54-7.52 (d, J=8 Hz, 1H), 4.05 (s, 3H); MS: MS m/z 242.0 (M++1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto get crude compound
  8. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-c7e2cbeb9b864a13b3fcdf0c44d0667d
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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