Ammonia → (E)-2-methyl-3-phenylacrylamide

Temperature

0 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of alpha-methylcinnamic acid (19.0 g, 116 mmol) and Et3N (17.1 mL, 122 mmol) in dry THF (500 mL) was treated with ethyl chloroformate (11.4 mL, 117 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min then aq. NH3 (250 mL) in THF (150 mL) was added. The reaction mixture was vigorously stirred at 0° C. for 30 min and at rt for 1 h30. The layers were then separated, the aq. layer extracted with CH2Cl2 (2×) and the combined organic extracts were concentrated under reduced pressure. The residue was partitioned between water and CH2Cl2, the layers separated and the aq. layer extracted with CH2Cl2 (2×). The combined org. extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound as a white solid. LC-MS-conditions 01: tR=0.75 min; [M+H]+=162.07.

1. stirringThe reaction mixture was vigorously stirred at 0° C. for 30 min and at rt for 1 h30
2. customThe layers were then separated
3. extractionthe aq. layer extracted with CH2Cl2 (2×)
4. concentrationthe combined organic extracts were concentrated under reduced pressure
5. customThe residue was partitioned between water and CH2Cl2
6. customthe layers separated
7. extractionthe aq. layer extracted with CH2Cl2 (2×)
8. dry with materialextracts were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-e42e0ad3d7f64f79896921483ed7a0e3

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563714B2