Water → HCID 178526838, compound

HRID 1622078Notes

Reaction equation

HRID 1622078 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Cl:11]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:11][C:7]1[C:2]([OH:1])=[N:3][CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 178526703HCID 178526703, compound

Product 1

HCID 178526838HCID 178526838, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-5-nitropyridine (50 g, 357 mmol) and N-chlorosuccinimide (55 g, 410 mmol) were suspended in anhydrous DMF (150 mL). The suspension was stirred at room temperature for 18 hours. The resulting homogeneous reaction mixture was diluted by the slow addition of water (750 mL), which resulted in a pale yellow precipitate. The solids were isolated via filtration and dried under high vacuum to provide 3-chloro-5-nitro-2-hydroxypyridine (59 g, 95% yield).

Workup

  1. customresulted in a pale yellow precipitate
  2. customThe solids were isolated via filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5f2d0c591d8b46b5bded61787b2dbda9
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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