Benzylamine → 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one

HRID 246

Reaction equation

HRID 246 reaction equation
NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(=O)O.CC(=O)O.C[O-].Cc1ccccc1.[Na+].[Pd].c1ccc(P(CCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1>O=C1NCCc2cc(NCc3ccccc3)ccc21

Participants

7

Reactant 2

HCID 7504BenzylamineHCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 672239156-benzylamino-3,4-dihydro-2H-isoquinolin-1-oneYield 0%

Reagents, catalysts & solvents 4

HCID 10942334Sodium MethoxideReagentHCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 4144353Palladium (II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a small MW* sealed test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (24.16 µl, 0.22 mmol), palladium(II) acetate (2.483 mg, 0.01 mmol), Ethylenebis(diphenylphosphine) (8.81 mg, 0.02 mmol) and sodium methoxide (13.14 mg, 0.24 mmol) in toluene (2188 µl) combined to give a orange suspension. Heated reaction to 100°C overnight. Took LCMS - No reaction, only see unreacted SM. Discarded reaction.

Sources & evidence

ORD record
ord-08bf18171af14ad9bb3d94faf7cd7b73
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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