2-Amino-4,6-dichloropyridine → HCID 178516185, compound

HRID 1820700Notes

Reaction equation

HRID 1820700 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[N:7]=1>O.S(=O)(=O)(O)O>[Cl:13][C:8]1[CH:9]=[C:10]([Cl:12])[CH:11]=[C:6]([OH:2])[N:7]=1

Participants

5

Reactant 2

HCID 53166492-Amino-4,6-dichloropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178516185HCID 178516185, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (64 mg, 0.93 mmol) dissolved in water (0.6 mL), was added dropwise to a stirred solution of 2-amino-4,6-dichloropyridine (prepared according to the method described in Recl. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5% sulphuric acid (aq) (5 mL) at 0° C., over 5 min. The mixture was stirred at 0° C. for 1 h and then diluted with water (20 mL) and extracted with DCM (3×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo to afford the 2,4-dichloro-6-hydroxypyridine (116 mg, 0.71 mmol, 92%) M.S. (ESI) (m/z) 164,166 [M+H]+.

Workup

  1. customprepared
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bb7bc7a37d7403381cb90d2b957b545
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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