Aniline → HCID 13115134, compound

HRID 2351569Notes

Reaction equation

HRID 2351569 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.B(F)(F)F.CCOCC.O1CCCC1.N[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:26]1([NH:10][C:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:9])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8000Boron trifluoride etherateHCID 8028TetrahydrofuranHCID 166410233-Methylpyridine-2-carboxamide

Product 1

HCID 13115134HCID 13115134, compoundYield 354.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-methyl-2-pyridinecarboxamide (15.0 o, 0.11 mole) are added BF3.OEt2 (14.0 mL, 0.11 mole) and tetrahydrofuran (75 mL). After about 5 minutes, aniline (10.3 g, 0.11 mole) is slowly added and the solution is heated at reflux for 5 hours. The reaction is cooled and diluted with water and the oroduct is extracted into ethyl acetate. The solvent is removed and the residue is purified by silica gel chromatography to give 8.32 g (0.39 mole, 35%) of N-phenyl-3-methyl-2-pyridinecarboxamide.

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction is cooled
  4. extractionthe oroduct is extracted into ethyl acetate
  5. customThe solvent is removed
  6. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f02a44f659274e69bf8aba5bfa649e16
Source dataset
uspto-grants-1989_10
Patent number
US04873335

Reaction notes

Loading…