Water → HCID 178526838, compound

HRID 2069899Notes

Reaction equation

HRID 2069899 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-d4316fe1a98a402d87dc4b493cf90250
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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