Acetic Acid → 2-[2-(1-Methoxyethylideneamino)-5-bromobenzoyl]pyridine

HRID 597351

反応式

HRID 597351 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].[C:17]([OH:20])(=O)[CH3:18].[CH:21]1C=CC=CC=1>>[CH3:21][O:20][C:17](=[N:1][C:2]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:18]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 241BenzeneHCID 738072-(2-Amino-5-bromobenzoyl)pyridine

生成物 1

HCID 214166192-[2-(1-Methoxyethylideneamino)-5-bromobenzoyl]pyridine

実験手順

A mixture of 8.7 g. of 2-(2-amino-5-bromobenzoyl)-pyridine, 5.7 g. of ortho-methyl acetate, 2.8 ml. of acetic acid and 100 ml. of benzene is refluxed, while removing alcohol produced by azeotropic distillation, for 1.5 hours and then cooled. The resultant mixture is washed with saturated aqueous sodium hydrogen carbonate solution, then with water, and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gives 2-[2-(1-methoxyethylideneamino)-5-bromobenzoyl]pyridine as an oily product. This product is dissolved in 60 ml. of methanol, and to the solution are added 44 ml. of hydrazine hydrate (100 %) and 1.9 ml. of acetic acid. After stirring at room temperature for 3 hours, the resulting precipitate is collected by filtration, washed with methanol and dried to give 3-amino-6-bromo-3,4-dihydro-4-hydroxy-2-methyl-4-(2-pyridyl)quinazoline as crystals. Recrystallization from a mixture of methanol and chloroform gives colorless crystals melting at 208° to 210° C. (decomposition).

後処理

  1. additionA mixture of 8.7 g
  2. customwhile removing alcohol
  3. customproduced by azeotropic distillation, for 1.5 hours
  4. temperaturecooled
  5. washThe resultant mixture is washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialwith water, and dried over sodium sulfate
  7. customEvaporation of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-b9b848398f324ab4bb882b6f24e5c837
出典データセット
uspto-grants-1977_03
特許番号
US04013763

関連ノート

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