Water → HCID 178526838, compound

HRID 1752851Notes

Reaction equation

HRID 1752851 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-74b80b55bcec453a9abca21d669fc170
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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