Pyridine → HCID 21906173, compound

HRID 1516393Notes

Reaction equation

HRID 1516393 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[N:14]1C=C[CH:17]=[CH:16][CH:15]=1.O=P(Cl)(Cl)[Cl:22].C(=O)(O)[O-].[Na+].[C:30](#[N:32])[CH3:31]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:32][C:30]1[CH:31]=[CH:17][C:16]([Cl:22])=[CH:15][N:14]=1)=[O:9]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6342AcetonitrileHCID 172865-Chloro-2-nitrobenzoic acidHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 21906173HCID 21906173, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 5-chloro-2-nitro-benzoic acid (100 g, 0.4962 mol) in acetonitrile (500 mL) was added pyridine (121 mL, 1.48 mol) at 25-30° C. The reaction mixture was then cooled to 0-10° C. under nitrogen atmosphere. To this was added POCl3 (54.6 mL, 0.5955 mol) drop wise by maintaining exothermicity. After stirring at 25-30° C. for 1 hr, reaction mixture was poured in cold water and filtered. Solid obtained was stirred in 500 mL of saturated solution of sodium bicarbonate for 10 min. Filtration and drying afforded 164 g of titled compound in 86% yield.

Workup

  1. temperatureby maintaining exothermicity
  2. customreaction mixture
  3. filtrationfiltered
  4. customSolid obtained
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-eff99a7f8ea943feaaf8c8adac2058dc
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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