1,2-Dichloroethane → N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide

HRID 25779노트

반응식

HRID 25779 반응식
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:15]([OH:23])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:24][CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[CH:34]=2)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=1.C(N(C(C)C)CC)(C)C>CCOC(C)=O.C(Cl)Cl>[CH3:43][O:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=[C:26]2[CH2:25][NH:24][C:15](=[O:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22566510HCID 22566510, 화합물

생성물 1

HCID 10408574N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide수율 22.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A round bottom flask equipped with a stir bar was charged with EDC (0.224 mmol, 1.1 equiv), HOBT (0.224 mmol, 1.1 equiv), benzoic acid (0.224 mmol, 1.1 equiv), 4-aminomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (0.204 mmol, 1 equiv) and 3.3 mL of methylene chloride. Diisopropyl ethyl amine (0.224 mmol, 1.1 equiv) was added last, the reaction was placed under argon, and stirred at room temperature overnight. The crude reaction mixture was transferred to a separatory funnel, diluted with EtOAc, and washed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine. The organics were concentrated in vacuo to afford a brown oil. The product was purified by column chromatography using silica gel eluting with a gradient of 10-50% EtOAc/hexanes. The product fractions were pooled and concentrated in vacuo to afford 18 mg of the title compound as a yellow oil.

후처리

  1. customA round bottom flask equipped with a stir bar
  2. customThe crude reaction mixture
  3. customwas transferred to a separatory funnel
  4. washwashed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine
  5. concentrationThe organics were concentrated in vacuo
  6. customto afford a brown oil
  7. customThe product was purified by column chromatography
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9e427c06399c41cbb4bb5db02dd0b691
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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