Hydrochloric Acid → HCID 67056852, compound

Temperature

-10 °C

To a solution of 3-amino-4-chlorobenzoic acid (3.99 g) in THF (35 mL) was added dropwise an 1 M THF solution of lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (46.5 mL) while keeping the internal temperature below −5° C. under a nitrogen atmosphere, and the mixture was stirred for 15 min around −10° C. Powder of methyl 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (3.46 g) was added to the mixture at once, and the resulted mixture was stirred at the same temperature for 3 hr under a nitrogen atmosphere. The reaction mixture was poured into a mixture of ice-water (700 mL) and 1 M HCl (100 mL), and the resulting mixture was extracted with EtOAc (150 mL×3). During the extraction, undissolved materials were produced, which were removed by filtration. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with MeOH, and the precipitates produced were collected by filtration to give 4-chloro-3-({[1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]carbonyl}amino)benzoic acid (1.74 g).

1. customthe internal temperature below −5° C.
2. stirringwas stirred at the same temperature for 3 hr under a nitrogen atmosphere
3. extractionthe resulting mixture was extracted with EtOAc (150 mL×3)
4. extractionDuring the extraction
5. customundissolved materials were produced
6. customwhich were removed by filtration
7. washThe combined organic layers were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customThe filtrate was evaporated in vacuo
11. customthe residue was triturated with MeOH
12. customthe precipitates produced
13. filtrationwere collected by filtration

ORD record

ord-9dc773bd34be428f93e4933a7e78e6a0

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173684B2