Dimethylformamide → 2-Chloro-5-nitropyridine-3-carboxylic acid

HRID 1914597Notes

Reaction equation

HRID 1914597 reaction equation
O[C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.S(Cl)([Cl:21])=O>>[Cl:21][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178524577HCID 178524577, compound

Product 1

HCID 125426642-Chloro-5-nitropyridine-3-carboxylic acidYield 68%

Conditions

Temperature
80 °C

Procedure

2-Hydroxy-5-nitro-nicotinic acid (2.7 mmol) in a mixture of N,N-dimethylformamide (2.7 mmol) and thionyl chloride (5 ml) was heated at 80° C. for 1 h. The mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added ice-water (20 ml) and with vigorous stirring a precipitate formed. The precipitate was filtered off and dried in a vacuum oven to give a white solid (68%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. additionTo the resulting residue was added ice-water (20 ml)
  4. customformed
  5. filtrationThe precipitate was filtered off
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-877ef2d5e2da43c3a88d5c36a2bcb0f3
Source dataset
uspto-grants-2013_12
Patent number
US08614212B2

Reaction notes

Loading…