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HCID 67097724、化合物 → Methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 471529
ノート
印刷プレビュー

反応式

HRID 471529 の反応式
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11](=[O:19])[C:10]=2[C:20]([O:22][CH3:23])=[O:21])=CC=1>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11](=[O:19])[C:10]=1[C:20]([O:22][CH3:23])=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 67097724HCID 67097724、化合物

生成物 1

HCID 658173Methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate収率 42.3%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Methyl 4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 68a) (0.841 g, 2.49 mmol) was dissolved in TFA (5 mL) and stirred at room temperature for 30 minutes. The TFA was removed under reduced pressure, and the residue was dissolved in dichloromethane, then precipitated out by adding excess diethyl ether. The resultant solid was collected by filtration, suspended in dichloromethane, and washed with concentrated sodium bicarbonate. The solid was collected to give methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (0.230 g, 42%) as a white solid. M.p.: 236° C. 1H NMR (400 MHz, DMSO-d6) δ 3.73 (s, 3H), 7.12 (t, J=8.0 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H), 7.52 (t, J=8.0 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.38 (bs, 2H), 10.88 (bs, 1H). MS 219 (MH+).

後処理

  1. customThe TFA was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customprecipitated out
  4. additionby adding excess diethyl ether
  5. filtrationThe resultant solid was collected by filtration
  6. washwashed with concentrated sodium bicarbonate
  7. customThe solid was collected

出典と根拠

ORDレコード
ord-690e0c90c22848ce83d027798f436bd9
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633186B2

反応ノート

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