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

HRID 442098

反応式

HRID 442098 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 formed by azeotropic distillation, for 1.5 hours and then cooled. The resultant is washed with saturated aqueous sodium hydrogen carbonate, then with water, and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gives 2-[2-(1-methoxyethylideneamino)-5-bromobenzoyl]-pyridine as oily product. This product is dissolved in 60 ml. methanolic solution and 44 ml. of hydrazine hydrate (100%) and 1.9 ml. of acetic acid are added to the solution. The mixture is stirred at room temperature for 3 hours and the precipitate formed 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. customwhile removing alcohol
  2. customformed by azeotropic distillation, for 1.5 hours
  3. temperaturecooled
  4. washThe resultant is washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialwith water, and dried over sodium sulfate
  6. customEvaporation of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-d8dd0a936b7445459bd1cac12bb8b18d
出典データセット
uspto-grants-1977_08
特許番号
US04044129

関連ノート

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