Benzylamine → 4-Benzylimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester

HRID 370032ノート

反応式

HRID 370032 の反応式
C(OC([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14](=O)[CH2:13][CH:12]1[CH3:26])=O)C1C=CC=CC=1.C([N:29]([CH2:32][CH3:33])CC)C.[CH2:34](N)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+]>[Ti](Cl)(Cl)(Cl)Cl.O.ClCCl>[CH2:34]([O:43][C:42]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14](=[N:29][CH2:32][C:33]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:26]=2)[CH2:13][CH:12]1[CH3:26])=[O:45])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

8

反応物 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 15480673Benzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

生成物 1

HCID 154806744-Benzylimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester収率 219.1%

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

6,7-Dimethoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (0.83 g, 2.3 mmol) was dissolved in a solution of triethylamine (2.2 mL, 2.3 mmol), benzylamine (0.55 mL, 5.1 mmol), and anhydrous dichloromethane (15 mL). This solution was stirred in a room temperature water bath as 2.5 mL of 1M solution of titanium tetrachloride (TiCl4) in dichloromethane (2.5 mmol) was slowly added. The reaction was allowed to stir at room temperature for 48 h. The reaction mixture was then poured into a stirred solution of water (50 mL) and potassium carbonate (10 g). After filtration, the filtrate was extracted with ethyl acetate (3×100 mL), the combined organic phases washed with water (100 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give the desired imine (1.12 g, ca. 100%). 1H NMR (CDCl3) δ 1.2 (d, 3H), 2.7-2.9 (m, 2H), 3.7 (s, 3H), 3.9 (s, 3H), 4.6 (d, 1H), 4.7 (d, 1H), 5.0-5.2 (m, 2H), 5.4 (d, 1H), 7.2-7.5 (m, 11H), 7.8 (s, 1H).

後処理

  1. additionwas slowly added
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic phases washed with water (100 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-001abd7707e8464aad8a22ca34492b08
出典データセット
uspto-grants-2000_10
特許番号
US06140342

反応ノート

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