Pyridine → HCID 727211, compound

Methyl 4-aminobenzoate (Aldrich, 5.0 g, 33 mmol) was dissolved in 120 mL of anhydrous methylene chloride containing pyridine (3.2 mL, 39.6 mmol) and dimethylaminopyridine (DMAP, 500 mg) was added. To the ice-cooled mixture was added methyl chloroformate (2.80 mL, 36.3 mmol) while stirring. The stirring was continued for 16 h at room temperature. The reaction was quenched with water (50 mL) and the organic layer separated. The aqueous layer was extracted with chloroform (50 mL). The combined organic extract was dried over sodium sulfate. The volatiles were evaporated on a rotoevaporator to give a residue, which was crystallized from chloroform-methanol. The white solid was separated, dried in air followed by drying in a pistol at acetone reflux in vacuo to give 4.95 g (71.7%) of methyl 4-(methoxycarbonyl)aminobenzoate, mp 177°-178° C.

1. additionwas added
2. customThe reaction was quenched with water (50 mL)
3. customthe organic layer separated
4. extractionThe aqueous layer was extracted with chloroform (50 mL)
5. extractionThe combined organic extract
6. dry with materialwas dried over sodium sulfate
7. customThe volatiles were evaporated on a rotoevaporator
8. customto give a residue, which
9. customwas crystallized from chloroform-methanol
10. customThe white solid was separated
11. customdried in air
12. dry with materialby drying in a pistol at acetone
13. temperaturereflux in vacuo

ORD record

ord-09e2094410004b7185b491e4b00df360

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05602277