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

HRID 1844023ノート

反応式

HRID 1844023 の反応式
[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

参加物

4

反応物 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 62350489HCID 62350489、化合物

生成物 1

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

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-9d08e412cefa4c37a30c73a81e9a6596
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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