Pyridine → HCID 26240658, compound

HRID 1859750Notes

Reaction equation

HRID 1859750 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24].N1C=CC=CC=1>O1CCCC1>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][CH:29]=[C:20]([NH:19][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 666404-Methoxy-3-nitrobenzoic acidHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 26240658HCID 26240658, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxy-3-nitrobenzoic acid (5.0 g, 25 mmol) was added to thionyl chloride (20 mL) under an inert atmosphere and stirred and heated to reflux. After 2 hours the mixture was stripped to dryness by rotary evaporator, and 2 portions of benzene were successively mixed with then stripped from the residue to leave a solid. This residue was dissolved in tetrahydro-furan (20 mL) and added dropwise to a stirred solution of methyl 3-aminobenzoate (3.83 g, 25 mmol) and pyridine (2 mL) cooled in an icebath. The mixture was allowed to warm to room temperature following the addition, then the solvent was removed under reduced pressure. The residue was suspended in 1N HCl, stirred, filtered off, and washed successively with 1N HCl, 1N NaHCO3 (2×), and water (2×). The resulting solid was boiled briefly in methanol (500 mL)then allowed to cool. Filtration afforded the product (8.0 g); m.p. 233-235° C., in sufficient purity for the next step.

Workup

  1. temperatureheated to reflux
  2. customAfter 2 hours the mixture was stripped to dryness by rotary evaporator, and 2 portions of benzene
  3. additionwere successively mixed
  4. customto leave a solid
  5. temperaturecooled in an icebath
  6. additionthe addition
  7. customthe solvent was removed under reduced pressure
  8. stirringstirred
  9. filtrationfiltered off
  10. washwashed successively with 1N HCl, 1N NaHCO3 (2×), and water (2×)
  11. temperatureto cool
  12. filtrationFiltration

Sources & evidence

ORD record
ord-a3d83c701b9d43bf8f5310ee8b0f343d
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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