Phosphorus oxychloride → HCID 90411313, compound

HRID 717388Notes

Reaction equation

HRID 717388 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][NH:13][C:14]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([O:8][C:9]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90410947HCID 90410947, compound

Product 1

HCID 90411313HCID 90411313, compound

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-(benzyloxy)-6-methyl-1,2-dihydroisoquinolin-1-one (100 mg, 0.38 mmol, 1.00 equiv) and POCl3 (10 mL). The resulting solution was heated to reflux for 3 h in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 250 mL of ethyl acetate. The resulting mixture was washed with 2×150 mL of water and 2×150 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). This resulted in 70 mg (96%) of 5-(benzyloxy)-1-chloro-6-methylisoquinoline as an off-white solid. MS (ESI) m/z 284 ([M+H]+).

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 3 h in an oil bath
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. additionThe resulting solution was diluted with 250 mL of ethyl acetate
  7. washThe resulting mixture was washed with 2×150 mL of water and 2×150 mL of brine
  8. dry with materialThe mixture was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThis resulted in 70 mg (96%) of 5-(benzyloxy)-1-chloro-6-methylisoquinoline as an off-white solid

Sources & evidence

ORD record
ord-5d3c49663f4a4e068c53924b84478565
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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