Hydrochloric Acid → 2-[(4-Bromophenoxy)methyl]nicotinic acid

HRID 226259Notes

Reaction equation

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

Participants

Conditions

Temperature: 165 °C

Procedure

32 g (185 mmol) of 4-bromophenol are treated in methanol with 33.32 g (185 mmol) of 30% solution of sodium methoxide in methanol. The solvent is eliminated and the residue mixed with 5.0 g (37.00 mmol) of furo[3,4-b]pyridin-5(7H)-one (prepared according to Synthesis, 1997, 113-116). The system is stirred at 165° C. for 30′ (at first the mixture melts, afterwards solidifies). Once at room temperature, the solid is dissolved in excess water, adjusted at pH 7-8 with 2N HCl and extracted two times with dichloromethane. The aqueous layer is adjusted at pH 5-6 with more 2N HCl and the solid that precipitates is filtered, washed with water and dried. The yield is 6.6 g (58%).

Workup

extractionextracted two times with dichloromethane
customthe solid that precipitates
filtrationis filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-2ac9279014114907a916be1f6da53216
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557212B2

Reaction notes

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