Dimethylformamide → HCID 178510366, compound

HRID 1370098Notes

Reaction equation

HRID 1370098 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)C=O.[OH:11][C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:15]([C:16]([NH2:18])=O)=[CH:14][N:13]=1>O>[C:16]([C:15]1[CH:19]=[C:20]([N+:21]([O-:23])=[O:22])[C:12]([OH:11])=[N:13][CH:14]=1)#[N:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178513756HCID 178513756, compound

Product 1

HCID 178510366HCID 178510366, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (2.99 mL) was added dropwise to N,N-dimethylformamide (49 mL) at 0° C., and the mixture was stirred at the same temperature for 15 minutes. Then 6-hydroxy-5-nitronicotinamide (4.9 g) was added portionwise to the mixture, and the reaction mixture was stirred at 50° C. for an hour. Water was added to the reaction mixture at 0° C., and the resulting precipitate was collected by filtration in vacuo. The obtained solid was washed with water to give 5-cyano-2-hydroxy-3-nitropyridine (3.17 g) as a pale brown solid.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for an hour
  2. filtrationthe resulting precipitate was collected by filtration in vacuo
  3. washThe obtained solid was washed with water

Sources & evidence

ORD record
ord-31c59caaa8a0418b879aa3975ec6842f
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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