Dichloromethane → HCID 65019042, compound

HRID 215833Notes

Reaction equation

HRID 215833 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CC(C)=O>[CH3:8][C:7]1[C:2]([O:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([O:13][CH3:12])=[O:22])=[CH:20][CH:19]=2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 65019042HCID 65019042, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of commercial 2-chloro-3-methyl-5-nitro-pyridine (0.5 g, 2.88 mmol), 4-hydroxy-benzoic acid methyl ester (0.45 g, 2.96 mmol) and K2CO3 (0.398 g, 2.90 mmol) in anhydrous acetone (20 ml) was refluxed for 15 h. After cooling to room temperature, the precipitate was filtered and washed with acetone (2×10 ml). The filtrates were concentrated at reduced pressure and the residue was purified by column chromatography (eluting with DCM/hexane 5:1 then DCM) to provide methyl 4-(3-methyl-5-nitropyridin-2-yloxy)benzoate (0.788 g, 95% yield).

Workup

  1. temperaturewas refluxed for 15 h
  2. filtrationthe precipitate was filtered
  3. washwashed with acetone (2×10 ml)
  4. concentrationThe filtrates were concentrated at reduced pressure
  5. customthe residue was purified by column chromatography (
  6. washeluting with DCM/hexane 5:1

Sources & evidence

ORD record
ord-85af5429c02f4fef9421db90b061fa45
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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