Hydrochloric Acid → 3-(2-Nitro-5-chlorothiophenoxy)isonicotinic acid
Reaction equation
N[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].N([O-])=O.[Na+].[OH-].[Na+].Cl.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23]([SH:25])[CH:24]=1>O>[N+:26]([C:22]1[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][C:23]=1[S:25][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9])([O-:28])=[O:27]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 53 °C
Procedure
A solution of 3-amino-4-carboxypyridine (1.4 g), sodium nitrite (0.81 g) and aqueous sodium hydroxide 2.9 M (13.3 ml) was added to a solution of aqueous hydrochloric acid 4.3 M (9.8 ml) while the temperature was maintained at 0-5 C. The mixture was stirred for 10 minutes and then added dropwise over the course of 2 hrs to a stirred mixture of 5-chloro-2-nitrothiophenol (2.34 g) and sodium hydroxide (2.63 g) in water (21 ml) maintained at about 53° C. (a brisk nitrogen evolution occurred). The mixture was stirred for 15 minutes, cooled to room temperature and filtered. The fitrate was made strongly acidic (pH=2) with hydrochloric acid 12 M and the precipitated solid was collected by filtration and dried to yield a brownish-orange solid (3 g). The solid was washed with dichloromethane:acetonitrile (30 ml) and dried to leave crude product (1.2 g). Crystallization from ethyl cellosolve led to the pure product, m.p. 280-281, °C.
Workup
- temperaturewas maintained at 0-5 C
- stirringThe mixture was stirred for 15 minutes
- temperaturecooled to room temperature
- filtrationfiltered
- filtrationthe precipitated solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-9bb85e2d19c04daf880c382803d7f939
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935969
Reaction notes
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