Triethylamine → 3-[2-Benzyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-acrolein

HRID 1741707

반응식

HRID 1741707 반응식
[CH2:1]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:21][CH:22](OC)[CH:23]=[CH2:24].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:24]=[CH:23][CH:22]=[O:21])[CH:14]=2)[C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 80145Acrolein dimethyl acetalHCID 80271Tri-o-tolylphosphineHCID 189639842-Benzyl-6-bromo-isoquinolin-1-one

생성물 1

HCID 539192843-[2-Benzyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-acrolein

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-benzyl-6-bromo-1,2-dihydro-1-oxoisoquinoline (1 g, 3.2 mmol), acrolein dimethyl acetal (2.6 mL, 22.4 mmol), Pd(OAc)2 (15 mg, 0.064 mmol), P(o-tolyl)3 (78 mg, 0.26 mmol) and Et3N (0.5 mL, 3.84 mmol) in DMF (2 mL) is heated in a sealed tube apparatus at 120° for 48 hours. After cooling to room temperature, the reaction mixture is diluted with EtOAc, filtered, washed with saturated NaCl solution, dried over MgSO4 concentrated in vacuo, and the residue is chromatographed (silica gel 1:4 EtOAc/hexane) to yield 3-[2-benzyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-acrolein.

후처리

  1. temperatureis heated in a sealed tube apparatus at 120° for 48 hours
  2. filtrationfiltered
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue is chromatographed (silica gel 1:4 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-1b40f671cefb4b60846d5f217aea54db
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334600

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