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

HRID 257051Notes

Reaction equation

HRID 257051 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bc6acf83e4354455a1b481c76c067174
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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