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 | |
| 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% |
| Binap, (A+-)-; Palladium (II) acetate | potassium 2-methylpropan-2-olate | 130 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
**Repeat 02915-84 but use NO solvent** In a 5 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (6.89 mg, 0.01 mmol) and palladium(II) acetate (2.483 mg, 0.01 mmol) combined to give a tan suspension. potassium tert-butoxide (24.82 mg, 0.22 mmol) was then added last. Placed test tube onto Smith MW* platform. Heated reaction to 70°C for 5 minutes. NO reaction!!! Added DMF (0.5 ml) and reheated reaction to 130°C for 15 mins. Took LCMS - no reaction, only unreacted SM!! Discarded reaction.
The source
This record comes from experimental reaction archive (ord-4a6bd61cd0ff477baa0ad5e567d741e9). Open the source and check it against what is on this page.
experimental reaction archive record ord-4a6bd61cd0ff477baa0ad5e567d741e9 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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