Ethyl 4,5-dihydro-4-oxo-5-phenylpyrano[3,2-b]indole-2-carboxylate → 4,5-Dihydro-4-oxo-5-phenylpyrano[3,2-b]indole-2-carboxylic acid

HRID 26160ノート

反応式

HRID 26160 の反応式
[O:1]=[C:2]1[C:7]2[N:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[O:5][C:4]([C:21]([O:23]CC)=[O:22])=[CH:3]1>C(O)(=O)C.Cl>[O:1]=[C:2]1[C:7]2[N:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[O:5][C:4]([C:21]([OH:23])=[O:22])=[CH:3]1

参加物

4

反応物 1

HCID 12628412Ethyl 4,5-dihydro-4-oxo-5-phenylpyrano[3,2-b]indole-2-carboxylate

生成物 1

HCID 126284294,5-Dihydro-4-oxo-5-phenylpyrano[3,2-b]indole-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

A mixture of 1.0 g (0.0033 mole) of ethyl 4,5-dihydro-4-oxo-5-phenylpyrano [3,2-b]indole-2-carboxylate in 10 ml glacial acetic acid and 2.0 ml conc. hydrochloric acid was stirred at reflux for 41/2 hr, then cooled and added to 75 g ice - H2O. The solid was filtered, washed with cold water, then added to a mixture of 35 ml 5% aqueous sodium carbonate and 250 ml water. After filtering by gravity, tha aqueous solution was washed three times with 75 ml chloroform, cooled in ice, and acidified with 4.0 N hydrochloric acid. The orange precipitate was filtered, digested 15 min on the steam bath with 25 ml water and re-filtered warm. Recrystallization from DMF-water yielded an off-white solid of mpt.>290°.

後処理

  1. temperatureat reflux for 41/2 hr
  2. temperaturecooled
  3. filtrationThe solid was filtered
  4. washwashed with cold water
  5. additionadded to a mixture of 35 ml 5% aqueous sodium carbonate and 250 ml water
  6. filtrationAfter filtering by gravity
  7. washtha aqueous solution was washed three times with 75 ml chloroform
  8. temperaturecooled in ice
  9. filtrationThe orange precipitate was filtered
  10. filtrationre-filtered
  11. temperaturewarm
  12. customRecrystallization from DMF-water
  13. customyielded an off-white solid of mpt
  14. custom>290°

出典と根拠

ORDレコード
ord-0a202b9cede1473991f009021cb0bc23
出典データセット
uspto-grants-1979_04
特許番号
US04148806

反応ノート

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