Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycerol | HCID 753 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | 5-Fluoro-2-methyl-3-nitroaniline | HCID 18465377 | — |
| Reactant | HCID 178526933 | HCID 178526933 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 18465378 | HCID 18465378 | — |
Reaction Steps
A mixture of 2-amino-4-fluoro-6-nitrotoluene (4.4 g), glycerin (7.5 g), arsenic(V) oxide hydrate (Aldrich, 54% in arsenic, 5.0 g), and concentrated sulfuric acid (35 mL) is heated to 140° C. for 4 hours. The reaction is allowed to cool to room temperature and diluted with water (300 mL). The mixture is basified with concentrated ammonium hydroxide to pH=10 and extracted with ethyl acetate (6×300mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The crude product is purified by flash chromatography on silica gel, eluting with 25% ethyl acetate/hexane to afford 7-amino-5-fluoro-8-methylquinoline as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05716966 |
|---|
| Source dataset | uspto-grants-1998_02 |
|---|
| ORD ID | ord-a755083ffb1c4408bc3db2bf5237cc6e |
|---|
| Source note | uspto-grants-1998_02 |
|---|
