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

HRID 257051

反応式

HRID 257051 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bc6acf83e4354455a1b481c76c067174
出典データセット
uspto-grants-1993_11
特許番号
US05260316

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