Water → 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1696526Notes

Reaction equation

HRID 1696526 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[NH:12][CH2:11][CH2:10]2)(=O)=O.[C:20](=[N:33][NH2:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:21]1([C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:33][NH:34][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[NH:12][CH2:11][CH2:10]3)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79304DiphenylmethylidenehydrazineHCID 534141981-Oxo-1,2,3,4-tetrahydroisoquinolin-6-YL trifluoromethanesulfonate

Product 1

HCID 866116856-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-oneYield 50%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

To a suspension of 1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate (1.70 g, 5.76 mmol), benzophenone hydrazone (1.36 g, 6.91 mmol), Cs2CO3 (2.81 g, 8.64 mmol) and DPPF (0.048 g, 0.086 mmol) in degassed PhMe (40 mL) was added Pd(OAc)2 (0.013 g, 0.058 mmol) and the resulting mixture was stirred at RT for 30 min and then heated at 90° C. After 16 h, the mixture was cooled to RT, H2O (50 mL) was added and the mixture was extracted with EtOAc (3×50 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one (980 mg, 50% yield). 1H NMR (400 MHz, acetone-d6): δ 8.69 (brs, 1H), 7.79 (d, J=9.2 Hz, 1H), 7.63-7.54 (m, 5H), 7.37-7.31 (m, 5H), 7.11-7.08 (m, 2H), 6.67 (brS, 1H), 3.47 (dt, J=7.2, and 3.2 Hz, 2H), 2.90 (t, J=6.6 Hz, 2H); MS (ESI) m/z: 342.0 (M+H+).

Workup

  1. temperatureheated at 90° C
  2. waitAfter 16 h
  3. temperaturethe mixture was cooled to RT
  4. extractionthe mixture was extracted with EtOAc (3×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-8056c0b9efb54381bae95ca07bb15800
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…