Sodium Hydroxide → 6-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid

HRID 1906110Notes

Reaction equation

[C:1]([C:4]([NH:9][C:10]([C:12]1[N:17]=[C:16]2[O:18][CH:19]=[CH:20][C:15]2=[CH:14][C:13]=1[C:21]([OH:23])=[O:22])=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[Na+]>O>[CH:5]([C:4]1([CH3:8])[C:1](=[O:3])[NH:2][C:10]([C:12]2[N:17]=[C:16]3[O:18][CH:19]=[CH:20][C:15]3=[CH:14][C:13]=2[C:21]([OH:23])=[O:22])=[N:9]1)([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution containing 6-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]furo[2,3-b]pyridine-5-carboxylic acid (3.8 g, 0.012 mol) in aqueous sodium hydroxide 2.4 g, 0.06 mol) in water (40 mL) is stirred at 65° C. for three hours. The reaction mixture is then heated at 75° C. for one hour, allowed to cool, poured into ice, acidified to pH 2-3 and the resulting solid filtered off and dried. Crystallization from an acetone-methanol mixture affords pure 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid mp 237°-244° C.

Workup

temperatureThe reaction mixture is then heated at 75° C. for one hour
temperatureto cool
additionpoured into ice
filtrationthe resulting solid filtered off
customdried
customCrystallization from an acetone-methanol mixture

Sources & evidence

ORD record: ord-3cd04d999cc74cbd881d6712b9203d77
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04650514

Reaction notes

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