Hydrochloric Acid → 4-((((Pyridin-3-ylmethoxy)carbonyl)amino)methyl)benzoic acid
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[OH-].[Na+].[NH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.[Cl-].[Na+].Cl.CN(C)[CH:27]=[O:28]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:27]([NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:20][CH:21]=2)=[O:28])[CH:2]=1Participants
Procedure
A N,N-dimethylformamide (150 ml) solution including 65.4 g (0.6 mole) of 3-pyridinemethanol was added dropwise to a N,N-dimethylformamide (300 ml) suspension including 97.2 g (0.6 mole) of N,N′-carbonyldiimidazole at an internal temperature of 10° C. or less. The mixture was then added dropwise to a separately prepared 1 N aqueous sodium hydroxide solution (455 ml) including 75.5 g (0.5 mole) of 4-aminomethylbenzoic acid, followed by stirring at room temperature for 6 hours. To the resultant reaction mixture, a saturated sodium chloride solution was added, and concentrated hydrochloric acid was further added, thereby neutralizing the solution. After aging at 5° C. for 2 hours, the deposited white solid was collected by filtration, washed with water and methanol, and then dried to obtain 140 g (yield: 98%) of 4-[N-(pyridin-3-ylmethoxycarbonyl)amino-methyl]benzoic acid.
Workup
- customat an internal temperature of 10° C. or less
- customTo the resultant reaction mixture
- waitAfter aging at 5° C. for 2 hours
- filtrationthe deposited white solid was collected by filtration
- washwashed with water and methanol
- customdried
Sources & evidence
- ORD record
- ord-83c497ba74ec46aaa344c693c217351d
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06320078B1
Reaction notes
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