Methanol → 7-Chloro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843819ノート

反応式

HRID 1843819 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O:17][C:18](=O)[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)C.CO>O=P(Cl)(Cl)Cl.C(Cl)Cl>[Cl:28][C:25]1[CH:26]=[C:27]2[C:22]([CH2:21][CH2:20][NH:19][C:18]2=[O:17])=[CH:23][CH:24]=1

参加物

6

反応物 3

HCID 887MethanolHCID 14812Phosphorus oxide (P4O10)HCID 15405334ethyl N-[2-(4-chlorophenyl)ethyl]carbamate

生成物 1

HCID 186723977-Chloro-3,4-dihydroisoquinolin-1(2H)-one収率 25,095.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24813Phosphorus oxychloride溶媒

実験手順

P2O5 (3.1 g, 0.0495 mmol) was added to a stirred solution of [2-(4-chloro-phenyl)-ethyl]-carbamic acid ethyl ester (2.5 g, 0.01097 mmol) in POCl3 (10 mL) The resulting mixture was heated to reflux for 3 hours. The reaction was monitored by TLC (10% methanol in DCM). The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The concentrate was quenched with chilled water, basified with NaHCO3 solution and extracted with ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (10% methanol in CHCl3) afforded 500 mg of the product (26.3% yield).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was quenched with chilled water
  5. extractionextracted with ethylacetate
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customPurification by column chromatography on silica gel (10% methanol in CHCl3)

出典と根拠

ORDレコード
ord-2b00c07b8df449f0af710961f22bf424
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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