Methanol → Methyl 4-amino-3-methylbenzoate

In a 300 mL three-necked, round-bottomed flask were dissolved 5.2 g (34.4 mmole) of 4-amino-3-methylbenzoic acid in 75 ml of anhydrous methanol. Anhydrous hydrogen chloride was bubbled into the flask for 3 to 5 minutes and the resulting solution was refluxed for 2 hours. The solvent was removed using a rotary evaporator, the resulting residue was introduced into a mixture of 200 ml of water and 100 ml of methylene chloride and the mixture was then separated into two phases. The aqueous layer was made basic with 10% aqueous sodium hydroxide and extracted with methylene chloride (3×100 ml). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent removed using a rotary evaporator yielding 5.68 g methyl 4-amino-3-methylbenzoate.

1. customAnhydrous hydrogen chloride was bubbled into the flask for 3 to 5 minutes
2. temperaturethe resulting solution was refluxed for 2 hours
3. customThe solvent was removed
4. customa rotary evaporator
5. additionthe resulting residue was introduced into a mixture of 200 ml of water and 100 ml of methylene chloride
6. customthe mixture was then separated into two phases
7. extractionextracted with methylene chloride (3×100 ml)
8. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
9. customthe solvent removed
10. customa rotary evaporator

ORD record

ord-4450bcd4d42043cdb236cbe3cf9160b3

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929098