Dichloromethane → 5,6-Dichloronicotinic acid

HRID 2293960Notes

Reaction equation

HRID 2293960 reaction equation
O[C:2]1C=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.O=S(Cl)[Cl:13].Cl[CH2:16][Cl:17]>CN(C=O)C>[Cl:13][C:2]1[C:16]([Cl:17])=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 178418479HCID 178418479, compound

Product 1

HCID 2479875,6-Dichloronicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

2-Hydroxypyridine-5-carboxylic acid (4 g, 29 mmol) was dissolved 150 mL of dichloromethane, 50 mL of SOCl2, and five drops of DMF. The raction mixture was heated to reflux under a nitrogen atmosphere for sixteen hours. The reaction mixture was evaporated to an oily solid and used without further purification or characterization (see Preparation 3).

Workup

  1. temperatureThe raction mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for sixteen hours
  3. customThe reaction mixture was evaporated to an oily solid
  4. customused without further purification or characterization (see Preparation 3)

Sources & evidence

ORD record
ord-b2a99d45a0c443ad8cb6451ca32bb4f7
Source dataset
uspto-grants-1997_11
Patent number
US05688796

Reaction notes

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