Buchwald–Hartwig amination: 4-Chlorotoluene → Methyl 2-methyl-2-[(4-methylphenyl)amino]propanoate
0% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 4-Chlorotoluene | C₇H₇Cl | |
| Reactant | Methyl 2-amino-2-methylpropanoate | C₅H₁₁NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Bis(adamantan-1-yl)(butyl)phosphane | C₂₄H₃₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 2-methyl-2-[(4-methylphenyl)amino]propanoate | C₁₂H₁₇NO₂ | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of Methyl 2-methyl-2-[(4-methylphenyl)amino]propanoate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
A flask was loaded with diacetoxypalladium (6.39 mg, 0.03 mmol), BUTYLDI-1-ADAMANTYLPHOSPHINE (0.020 g, 0.06 mmol), sodium 2-methylpropan-2-olate (0.164 g, 1.71 mmol) and methyl 2-amino-2-methylpropanoate (0.2 g, 1.71 mmol). The flask was evacuated and backfilled and toluene (5ml) and 1-chloro-4-methylbenzene (0.168 ml, 1.42 mmol) was added.The mixture was stirred for 20h at 120°. No conversion of startingmaterial was observed.
The source
This record comes from experimental reaction archive (ord-adf0259dd1b4403cabef49044d700c84). Open the source and check it against what is on this page.
experimental reaction archive record ord-adf0259dd1b4403cabef49044d700c84 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.
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Where to next
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