Phosphorus oxide (P4O10) → 6-Methyl-3,4-dihydroisoquinolin-1(2H)-one

HRID 1844023Notes

Reaction equation

HRID 1844023 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][CH2:6][NH:7][C:8](=O)[O:9]CC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O=P(Cl)(Cl)Cl>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:8](=[O:9])[NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 62350489HCID 62350489, compound

Product 1

HCID 228908916-Methyl-3,4-dihydroisoquinolin-1(2H)-oneYield 19%

Procedure

Ethyl 3-methylphenethylcarbamate (I-69c: 13.5 g, 65.217 mmol) was reacted with P2O5 (18.51 g, 130.434 mmol) and POCl3 (135 mL) at 110° C. for 1 hour. The reaction mass was concentrated under reduced pressure, quenched with ice, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 2 g of the product (19% yield). LCMS: 75.24%, m/z=162.3 (M+1)

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customquenched with ice
  3. extractionextracted
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (1% methanol in DCM)

Sources & evidence

ORD record
ord-9d08e412cefa4c37a30c73a81e9a6596
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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