Pyridine → Methyl 3-chloro-4-methylcarbanilate

To a stirred solution of 10.0 grams (0.071 mole) of 3-chloro-4-methylaniline in 100 ml of chloroform was added 16.7 grams (0.212 mole) of pyridine. Methyl chloroformate, 8.0 grams (0.085 mole), was then added dropwise during a 20 minute period. During the addition the reaction mixture temperature was held between 25°-30° C. with external cooling. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was washed into a separatory funnel with 50 ml of chloroform; and the solution was washed with two 100 ml portions of water and 100 ml of aqueous 5% hydrochloric acid. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a waxy solid residue. The residue was recrystallized from hexane/ethyl acetate to give 10.9 grams of methyl(3-chloro-4-methylphenyl)carbamate; m.p. 80°-81.5° C.

1. additionDuring the addition the reaction mixture temperature
2. customwas held between 25°-30° C. with external cooling
3. additionUpon completion of addition the reaction mixture
4. washThe reaction mixture was washed into a separatory funnel with 50 ml of chloroform
5. washand the solution was washed with two 100 ml portions of water and 100 ml of aqueous 5% hydrochloric acid
6. dry with materialThe organic layer was dried with magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure to a waxy solid residue
9. customThe residue was recrystallized from hexane/ethyl acetate

ORD record

ord-f767c71a14fe4b4eb818c99a30ff4c5b

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04552585