Sodium Hydroxide → HCID 178524772, compound

HRID 1815885Notes

Reaction equation

C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:19])[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([OH:20])=[N:6][CH:5]=1.[OH-].[Na+]>CO>[CH2:12]([NH:11][C:10]([C:8]1[C:7]([OH:20])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:21])=[O:2])=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 5-Benzylcarbamoyl-6-hydroxy-nicotinic acid methyl ester in methanol (20 ml) was added 5.2 ml (5.2 mmol) 1N NaOH. The mixture was heated to 50° C. and stirred overnight. Additional 1N NaOH was added (8.0 ml, 8.0 mmol). The mixture was heated to reflux for 6 hours. The mixture was allowed to cool and was stirred overnight. Methanol was removed by concentrating at reduced pressure. The resulting residue was dissolved in H2O and extracted with diethyl ether. The aqueous layer was acidified with 1M HCl and filtered. The solid product was washed with water and dried at reduced pressure overnight at 55° C. 1.2 g (85% yield). MS: m/z (APCI, AP+) 373.0 [M.]+. CHN Analysis: Calcd: C, 61.76; H, 4.44; N, 10.29. Found: C, 61.41; H, 4.42; N, 9.98.

Workup

temperatureThe mixture was heated
temperatureto reflux for 6 hours
temperatureto cool
stirringwas stirred overnight
customMethanol was removed
concentrationby concentrating at reduced pressure
dissolutionThe resulting residue was dissolved in H2O
extractionextracted with diethyl ether
filtrationfiltered
washThe solid product was washed with water
customdried at reduced pressure overnight at 55° C

Sources & evidence

ORD record: ord-f788f7685f7243588d1812b7506bda4c
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881743B2

Reaction notes

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