Chlorosuccinimide → tert-Butyl 6-chloro-5-hydroxypyridine-3-carboxylate

HRID 1271639Notes

Reaction equation

HRID 1271639 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:15]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[C:11]([OH:13])[C:10]([Cl:15])=[N:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 53432596tert-Butyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 53432597tert-Butyl 6-chloro-5-hydroxypyridine-3-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The compound of Example 52A (400 mg, 2.05 mmol) was dissolved in DMF (2 mL) and N-chlorosuccinimide (328 mg, 2.46 mmol) was added. The mixture was heated to 80° C. overnight, concentrated and purified by column chromatography to give the chloro pyridine (234 mg, 50%). MS (DCI) m/z 230, 232 (M+H+).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-886b7ce855844a90a230cf672116d62d
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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