Methane → HCID 13754284、化合物

HRID 1249506ノート

反応式

HRID 1249506 の反応式
[H-].[Na+].[C:3]([CH:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]1S(C1C=CC=CC=1)(=O)=O)#[N:4].C>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[C:3]([C:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1)#[N:4]

参加物

6

反応物 3

HCID 297MethaneHCID 24758Sodium hydrideHCID 137542791,2-Dihydro-5-methoxy-2-(phenylsulfonyl)-1-isoquinolinecarbonitrile

生成物 1

HCID 13754284HCID 13754284、化合物

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (1.2 g of 60% in mineral oil) is added to a stirred suspension of 1-cyano-2-benzenesulfonyl-1,2-dihydro-5-methoxyisoquinoline (10 g) in xylene (100 ml). The reaction mixture is refluxed under nitrogen for 3 hrs, cooled to RT, stirred for an additional hour, and filtered. The filtered solid is washed with xylenes. The filtrate is evaporated in vacuo. The filtered solid is stirred with methylene chloride and aqueous 5% sodium hydroxide solution. The methylene chloride phase is combined with the residue from the evaporated filtrate and the combined extracts are washed with 5% sodium hydroxide solution, H2O and dried over sodium sulfate. The dried extract is filtered and the filtrate evaporated in vacuo, affording a moist solid which is triturated in hexanes. The triturated solid is filtered, washed with hexanes, and dried, affording a fluffy orange solid, M.P. 166°-175° C. The crude product is dissolved in ethyl acetate, treated with charcoal, filtered and recrystallized from ethyl acetate, affording the desired cyanoisoquinoline as a crystalline solid, M.P. 180°-182° C.

後処理

  1. temperatureThe reaction mixture is refluxed under nitrogen for 3 hrs
  2. filtrationfiltered
  3. washThe filtered solid is washed with xylenes
  4. customThe filtrate is evaporated in vacuo
  5. stirringThe filtered solid is stirred with methylene chloride and aqueous 5% sodium hydroxide solution
  6. washthe combined extracts are washed with 5% sodium hydroxide solution, H2O
  7. dry with materialdried over sodium sulfate
  8. extractionThe dried extract
  9. filtrationis filtered
  10. customthe filtrate evaporated in vacuo
  11. customaffording a moist solid which
  12. customis triturated in hexanes
  13. filtrationThe triturated solid is filtered
  14. washwashed with hexanes
  15. customdried
  16. customaffording a fluffy orange solid, M.P. 166°-175° C
  17. filtrationfiltered
  18. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-0ecd65e678344091b4177dc2c655df50
出典データセット
uspto-grants-1986_12
特許番号
US04632927

反応ノート

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