HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 2-Chloro-7-fluoroquinoline-3-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | N-(3-Fluorophenyl)acetamide | HCID 9594 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Chloro-N,N-dimethylformiminium chloride | HCID 77311 | — |
| Product | 2-Chloro-7-fluoroquinoline-3-carbaldehyde | HCID 12099179 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A Vilsmeier reagent prepared from DMF (23 mL) and phosphoryl chloride (78.4 mL) at 0-10° C. is slowly added dropwise to 3-fluoroacetanilide (18.5 g, 0.12 mol) and the resulting mixture is stirred at 100° C. for 14 hours. The mixture is poured onto ice-water and extracted with CH2Cl2 twice. The combined organic layer is dried, filtered and concentrated. The crystal is collected and washed with CH2Cl2 to give 2-chloro-7-fluoroquinoline-3-carbaldehyde as a brown powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410275B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-5097097849bb41509046f41c77862573 |
| Source note | uspto-grants-2013_04 |