Thionyl Chloride → HCID 19781717, compound

HRID 257784Notes

Reaction equation

HRID 257784 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[NH:7][C:8]1[C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:3])=[O:2].S(Cl)([Cl:22])=O>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[NH:7][C:8]1[C:13]([C:14]([Cl:22])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 126276212-(3-Nitroanilino)-3-carboxypyridine

Product 1

HCID 19781717HCID 19781717, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(3-Nitroanilino)-3-carboxypyridine (66.3 g, 256 mmole) was suspended in benzene (1100 ml). To this suspension, thionyl chloride (66.3 ml) was added dropwise with stirring. The reaction mixture was refluxed for 4 hours. Excess solid material was filtered from the solution while the solution was still hot. The solvent was stripped from the solution and 69.7 g (251 mmole, 98% yield) of crude 2-(3-nitroanilino)-3-chloroformylpyridine (i.e., an acid chloride) as a solid was recovered, which was taken to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. filtrationExcess solid material was filtered from the solution while the solution

Sources & evidence

ORD record
ord-0e0bcc8b73aa4d14a26fe5d1dd28683a
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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