Cuminaldehyde → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-isopropylphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 908017노트

반응식

HRID 908017 반응식
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:3].[CH:23]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([CH3:25])[CH3:24].[O-:34][CH2:35][CH3:36].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9]2[CH:30]([C:29]3[CH:32]=[CH:33][C:26]([CH:23]([CH3:25])[CH3:24])=[CH:27][CH:28]=3)[C:35](=[O:34])[C:36]3[C:16]([C:15]([O:14][CH2:13][CH3:12])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:3]

참가 물질

6

반응물 4

HCID 326CuminaldehydeHCID 702EthanolHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208, 화합물

생성물 1

HCID 67261946Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-isopropylphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate수율 22%

시약·촉매·용매 1

HCID 7749Ethyl Propionate용매

반응 조건

온도
0 °C

실험 절차

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (588 mg, 2 mmol) and 4-isopropylbenzaldehyde (296 mg, 2 mmol) in ethyl propionate (15 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (138 mg, 6 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was then purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the title compound (210 mg, yield 22%). LC-MS (ESI) m/z: 471 (M+1)+.

후처리

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (100 mL×4)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas then purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-fb55af07ebc6485db29651832d4defbe
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012976B2

반응 노트

불러오는 중…