Ammonia → furo(3,4-b)pyridin-5(7H)-one

HRID 280059

反応式

HRID 280059 の反応式
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([O:5][C:6]2=[O:11])=O.C(N1C2C(=CC=CC=2)C=C1C)C.C(N(C1C=C(OCC)C=CC=1)CC)C.C(OC(=O)C)(=O)C.N>[Cl-].[Zn+2].[Cl-].C(O)(C)C.O.C(O)(=O)C>[C:6]1([C:7]2[C:2](=[N:1][CH:10]=[CH:9][CH:8]=2)[CH2:3][O:5]1)=[O:11]

参加物

10

反応物 5

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 74625N,N-Diethyl-m-phenetidineHCID 1704321H-Indole, 1-ethyl-2-methyl-

生成物 1

HCID 819439furo(3,4-b)pyridin-5(7H)-one収率 258.8%

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

20.0 g of quinolinic anhydride, 80 ml of acetic acid, 20.3 g of N-ethyl-2-methylindole and 2.74 g of zinc chloride are stirred at 20° C. for 5 hours. 23.6 g of 3-(N,N-diethylamino)-phenetole and 30 ml of acetic anhydride are then added, after which the reaction mixture is warmed to 50° to 60° C. and stirred at this temperature for 2 hours. After addition of 170 ml of 30% aqueous ammonia and 100 ml of water, the product precipitates as a paste and is isolated. 160 ml of isopropanol are added to the paste and the mixture is refluxed for 1 hour. After cooling, the recrystallised product is filtered off, washed with isopropanol and dried, affording 46.9 g of the isomer-free 4-azaphthalide compound of the formula ##STR15## of melting point 156° to 158° C.

後処理

  1. temperatureafter which the reaction mixture is warmed to 50° to 60° C.
  2. customthe product precipitates as a paste
  3. customis isolated
  4. temperaturethe mixture is refluxed for 1 hour
  5. temperatureAfter cooling
  6. filtrationthe recrystallised product is filtered off
  7. washwashed with isopropanol
  8. customdried

出典と根拠

ORDレコード
ord-96ff3c0d8cde44bca4cbc6c9fb34e7c3
出典データセット
uspto-grants-1986_05
特許番号
US04587539

関連ノート

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