Hydrochloric Acid → 4-(Methylamino)-3-nitrobenzoic acid

Methyl 4-(methylamino)-3-nitrobenzoate (1.82 g, 8.66 mmol) was dissolved in a 1:1 ratio of tetrahydrofuran (THF) (41.4 mL) and water (41.4 mL). To this was added lithium hydroxide (1.817 g, 43.3 mmol) and the reaction stirred at r.t. for 16 h. The reaction mixture was cooled to 0° C. and acidified by the addition of 5M HCl (˜20 mL, until the pH reached ˜5)—a bright yellow precipitate formed, the slurry was filtered and the residue washed with distilled H2O (2×30 mL). The residue was collected and dried in vacuo at 50° C. to afford the product as a yellow solid (1.43 g, 7.29 mmol, 84% yield). This was used without further purification in the subsequent reactions.

1. temperatureThe reaction mixture was cooled to 0° C.
2. customformed
3. filtrationthe slurry was filtered
4. washthe residue washed with distilled H2O (2×30 mL)
5. customThe residue was collected
6. customdried in vacuo at 50° C.

ORD record

ord-4f69701b96b649cbaf8e046277acc93a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09127003B2