Buchwald–Hartwig amination: 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one → 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one
0% yield, run at 130 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one | C₉H₈BrNO | |
| Reactant | Benzylamine | C₇H₉N | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one | C₁₆H₁₆N₂O | 0% |
Conditions
- Temperature
- 130 °C
Yield
- 0% of 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,2-Bis(diphenylphosphino)ethane; Palladium (II) acetate | sodium methanolate | Toluene | 110 °C | — | 0% |
| Binap, (A+-)-; Palladium (II) acetate | potassium 2-methylpropan-2-olate | Dimethylformamide | 130 °C | — | 0% (this run) |
| Binap, (A+-)-; Palladium (II) acetate | potassium 2-methylpropan-2-olate | 130 °C | — | 0% |
Procedure
Copied from the source record, unedited
**Repeat 02915-84 but use MW* only. Reduce benzylamine from 4 to 2 eqs.** In a 10 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.44 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (13.77 mg, 0.02 mmol) and palladium(II) acetate (4.97 mg, 0.02 mmol) in DMF (500 mL) combined to give a tan suspension. potassium tert-butoxide (49.6 mg, 0.44 mmol) was then added last. Placed test tube onto Smith MW* platform. Heated reaction to 130°C for 15 minutes. Reaction know a cloudy pale amber. Took LCMS - there is NO product present, ALL SM!!! Placed sealed test tube in heated (130°C) oil bath over weekend. Took LCMS - all SM is consumed but NO desired product is seen!!! Discarded reaction.
The source
This record comes from experimental reaction archive (ord-77ff9a88bff94b57b6f8498de8922bdf). Open the source and check it against what is on this page.
experimental reaction archive record ord-77ff9a88bff94b57b6f8498de8922bdf from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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