Water → HCID 281704, compound

To methyl 5-methoxy-6-methyl-pyridine-2-carboxylate (1.00 g, 5.52 mmol) was dissolved in tetrahydrofuran (5.4 mL) was added water (2.7 mL) and LiOH (132.2 mg, 5.52 mmol). The mixture was stirred at room temperature overnight, then at 60° C. for 1.5 hours. Additional LiOH in water (2.76 mL of 2 M, 5.519 mmol) was added and the reaction was heated at 60° C. for 0.5 hours. The mixture was poured into water (5 mL) and ethyl acetate (15 mL) and the layers were separated. The aqueous layer was acidified to pH 4 with 2 N HCl and was extracted with ethyl acetate (7×25 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 5-methoxy-6-methylpicolinic acid (0.71 g, 77%) as a white solid. 1H NMR (400 MHz, DMSO) δ 12.71 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.43 (d, J=8.5 Hz, 1H), 3.89 (s, 3H), 2.40 (s, 3H). ESI-MS m/z calc. 167.1, found 168.3 (M+1)+; Retention time: 0.19 minutes (3 min run).

1. waitat 60° C. for 1.5 hours
2. temperaturethe reaction was heated at 60° C. for 0.5 hours
3. customthe layers were separated
4. extractionwas extracted with ethyl acetate (7×25 mL)
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. customthe solvent was evaporated under reduced pressure

ORD record

ord-2546db4166054864893b7fb47e28ee19

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365588B2