Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | HCID 66700221 | HCID 66700221 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66700039 | HCID 66700039 | 48.5% |
Reaction Steps
[Step 3] 675 mg (approx. 1.98 mmol) of the benzyl-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinolin-8-yl carbamate were dissolved in 15 mL of dichloromethane followed by adding 313 mg (4.0 mmol) of pyridine. 234 mg (3.0 mmol) of acetyl chloride were further added followed by stirring for 30 minutes at room temperature. Following completion of the reaction, aqueous hydrochloric acid (1 mol/L) was added followed by extraction with chloroform. The organic phase was washed with water and then dehydrated with anhydrous sodium sulfate. The solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 2:1) to obtain 367 mg of benzyl-5-acetyl-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-8-yl carbamate in the form of a pale brown oil (56%, 2 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08604030B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-36ee50985d494a48b0b9348df20e88e0 |
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| Source note | uspto-grants-2013_12 |
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