Ammonia → HCID 14991375, compound

Temperature

140 °C

A mixture of 2-chloro-4,6-dimethylquinoline (3.8 g, prepared as described in note q above) and phenol (14 g) was heated to 140° C. and dry ammonia gas was passed into the stirred mixture for 3 hours. After cooling the mixture was dissolved in an aqueous potassium hydroxide solution (10% w/v) and extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with aqueous N sodium hydroxide solution, dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on a silica gel column using a 1:7 v/v mixture of methanol and ethyl acetate as eluent. There was thus obtained 2-amino-4,6-dimethylquinoline (0.4 g). A mixture of this product (0.4 g) and acetic anhydride (10 ml) was stirred at 20° C. for 3 hours and then evaporated to dryness. The residue was washed with petroleum ether (b.p. 60°-80° C., 3×25 ml) to leave 2-acetamido-4,6-dimethylquinoline as a pink solid (0.37 g).

1. temperatureAfter cooling the mixture
2. extractionextracted with ethyl acetate (3×50 ml)
3. washThe combined organic extracts were washed with aqueous N sodium hydroxide solution
4. dry with materialdried (magnesium sulphate)
5. customevaporated
6. customThe residue was purified by chromatography on a silica gel column
7. additiona 1:7 v/v mixture of methanol and ethyl acetate as eluent
8. additionA mixture of this product (0.4 g) and acetic anhydride (10 ml)
9. customevaporated to dryness
10. washThe residue was washed with petroleum ether (b.p. 60°-80° C., 3×25 ml)

ORD record

ord-8e8f1ed246c24a639ac2422a3a43fe11

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05112837