m-(Trifluoromethyl)nitrobenzene → HCID 15789206, compound

HRID 976933Notes

Reaction equation

HRID 976933 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[OH-].[Na+]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7386m-(Trifluoromethyl)nitrobenzeneHCID 104392-AminopyridineHCID 14798Sodium Hydroxide

Product 1

HCID 15789206HCID 15789206, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.91 g (10 mmol) of 3-nitrobenzotrifluoride, 1.88 g (20 mmol) of 2-aminopyridine and 1.2 g (30 mmol) of sodium hydroxide in the form of microbeads are heated at 50° C. for 6 h in 30 ml of abs. DMSO while passing through dry air. After cooling, the mixture is diluted with ethyl acetate and extracted several times by shaking with water. After drying and stripping off the organic solvent, 3.8 g of crude product are obtained which is purified by chromatography on silica gel using petroleum ether and ethyl acetate (volume ratio 1:1). 2.3 g (8.1 mmol, 81%) of 2-(4-nitro-2-trifluoromethylphenylamino)-pyridine of m.p. 83°-84° C. are thus obtained.

Workup

  1. customthrough dry air
  2. temperatureAfter cooling
  3. additionthe mixture is diluted with ethyl acetate
  4. extractionextracted several times
  5. customAfter drying
  6. customare obtained which
  7. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-77e4ab4452b649b79026e5fbba15c348
Source dataset
uspto-grants-1997_03
Patent number
US05612483

Reaction notes

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