4-Nitroaniline → 2-Methyl-N-(4-nitrophenyl)prop-2-enamide

Into a reaction vessel fitted with a cooling pipe, a stirrer, a thermometer and a nitrogen feed pipe, 50 parts of 4-nitroaniline, 40 parts of triethylamine and 525 parts of chloroform were fed, and then cooled to 5° C. or below. While the reaction solution obtained was kept at 5° C. or below, a solution prepared by dissolving 41 parts of methacrylic acid chloride in 30 parts of chloroform was dropwise added thereto. After its addition made dropwise was completed, the reaction solution was heated to room temperature, and, as it was, the reaction was carried out for 4 hours. After the reaction was completed, the organic phase formed was washed with 200 parts of ion-exchanged water. This organic phase was then dried with sodium sulfate, and thereafter the solvent was evaporated off under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 22 parts of an intermediate N-(4-nitrophenyl)methacrylamide (yield: 31%).

1. customInto a reaction vessel fitted with a cooling pipe, a stirrer
2. temperaturecooled to 5° C. or below
3. customWhile the reaction solution obtained
4. customwas kept at 5° C. or below
5. customa solution prepared
6. additionwas dropwise added
7. additionAfter its addition
8. customthe organic phase formed
9. washwas washed with 200 parts of ion-exchanged water
10. dry with materialThis organic phase was then dried with sodium sulfate
11. customthe solvent was evaporated off under reduced pressure
12. customThe residue obtained
13. customwas purified by silica gel column chromatography

ORD record

ord-ad89902745e148efb33a538349f20fc5

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09250552B2