Hydrochloric Acid → Ethyl 7-aminoquinoline-3-carboxylate

HRID 51971

反応式

HRID 51971 の反応式
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([N:17]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH:11]=2)=[O:6])[CH3:3]>C(O)C>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([NH2:17])[CH:11]=2)=[O:6])[CH3:3]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 102872307-(Benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 9877801Ethyl 7-aminoquinoline-3-carboxylate収率 68.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Concentrated hydrochloric acid (1 mL, 2.5 volumes) was added to a solution of 7-(benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester (400 mg, 1.05 mmol, 1 equiv) in ethanol (4 mL, 10 volumes). The solution was stirred at room temperature for three hours and then concentrated. The residue was dissolved in ethyl acetate (20 mL, 50 volumes) and the organic layer was washed with 1 N hydrochloric acid (5×25 mL). The pH of the combined aqueous layer was then adjusted to about 8 with solid sodium hydroxide. The aqueous layer was then extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to provide 7-amino-quinoline-3-carboxylic acid ethyl ester (155 mg, 68%) as a yellow solid. The crude solid can be further purified by flash column chromatography using silica gel (EM Science, Gibbstown, N.J., 230-400 mesh) in 60% ethyl acetate in hexanes if desired.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (20 mL, 50 volumes)
  3. washthe organic layer was washed with 1 N hydrochloric acid (5×25 mL)
  4. extractionThe aqueous layer was then extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-194726897d924469839c471fea67f027
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

関連ノート

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