Phosphorus oxychloride → HCID 71742713, compound

HRID 1852246Notes

Reaction equation

HRID 1852246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][CH:7]=[C:6]2[N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 709790426-Methoxy-4-(4-methyl-1-piperazinyl)-1(2H)-isoquinolinone

Product 1

HCID 71742713HCID 71742713, compoundYield 27.8%

Procedure

A solution of 6-methoxy-4-(4-methylpiperazin-1-yl)isoquinolin-1(2H)-one (0.16 g, 0.585 mmol) in POCl3 (5 ml) was refluxed for overnight. 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 (10% MeOH in CHCl3) to get desired compound (0.05 g, 27.8%) as solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.18-8.15(d, J=12 Hz, 1H), 7.92 (s, 1H), 7.45-7.42 (d, J=12 Hz, 1H), 7.36 (s, 1H), 3.97 (s, 3H), 3.09 (m, 4H), 2.52 (m, 4H), 2.31 (s, 3H); MS: MS m/z 292.15 (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 (10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-0aadb64bc0c34025a34d1e1dd5318ac3
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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