2-Chloro-3-nitropyridine → HCID 58577473, compound

HRID 82502Notes

Reaction equation

HRID 82502 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1>CN1C(=O)CCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 4591052-(p-Aminoanilino)benzoxazole

Product 1

HCID 58577473HCID 58577473, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-(1,3-benzoxazol-2-yl)benzene-1,4-diamine (0.50 g) and 2-chloro-3-nitropyridine (0.352 g) in NMP (3.0 ml) was stirred at 140° C. for 1.5 h. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 ml), and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride) to afford N-(1,3-benzoxazol-2-yl)-N′-(3-nitropyridin-2-yl)benzene-1,4-diamine (0.335 g) as a red solid.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-fde67ac8e4bd44129f6bc1ce06a7c7a7
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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