Hydrochloric Acid → 2-Nitro-5-(4-oxo-4H-pyridin-1-yl)-aniline

HRID 1488957Notes

Reaction equation

HRID 1488957 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[OH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[OH-].[K+].Cl>CS(C)=O>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:16]2[CH:17]=[CH:18][C:13](=[O:12])[CH:14]=[CH:15]2)=[CH:8][C:6]=1[NH2:7])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 742185-Chloro-2-nitroanilineHCID 178418642HCID 178418642, compound

Product 1

HCID 229035772-Nitro-5-(4-oxo-4H-pyridin-1-yl)-anilineYield 102.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

First, 8.628 g of 5-chloro-2-nitroaniline, 7.161 g of 4-hydroxypyridine, and 4.892 g of powdered potassium hydroxide were added to 60 ml of dry dimethylsulfoxide The mixture thus obtained was stirred at 130° C. for 3 hours in a nitrogen atmosphere. Then, 200 ml of ice water was added to the reaction mixture and neutralized with 4N hydrochloric acid. The resultant solution was stirred for 30 minutes, giving a precipitate. The precipitate was filtered and washed with water. The precipitate was subjected to silica gel column chromatography, and fractions eluted with 20% methanol in methylene chloride were collected. The collected fractions were combined and evaporated. The residue was recrystallized in methanol to give 11.868 g of yellowish orange crystals of 2-nitro-5-(4-oxo-4H-pyridin-1-yl)-aniline.

Workup

  1. customthus obtained
  2. customgiving a precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. washeluted with 20% methanol in methylene chloride
  6. customwere collected
  7. customevaporated
  8. customThe residue was recrystallized in methanol

Sources & evidence

ORD record
ord-2c6eaba6f7254a35b59bea23d6936358
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Reaction notes

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