Aniline → HCID 22406920, compound

HRID 2259630Notes

Reaction equation

HRID 2259630 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C(C)=CC=CC=1>[C:12]1([NH:11][C:8]([C:5]2[CH:6]=[N:7][C:2]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:3][CH:4]=2)=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 792226-Chloronicotinic acid

Product 1

HCID 22406920HCID 22406920, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

6-Chloro-3-pyridinecarboxylic acid (15.76 g, 0.1 mole) and aniline (9.3 g, 0.1 mole) were heated together in 50 mL xylene at 180°-185° C. (oil bath) for 3 hours. After cooling, the solid that formed was filtered and washed with Et2O. The solid was triturated with NaHCO3 solution (pH 8), then filtered to give 7.0 g (24%) of N-phenyl-6-(phenylamino)-3-pyridinecarboxamide. The aqueous NaHCO3 solution was carefully neutralized with glacial HOAc (pH 6), and the solid that precipitated was filtered and washed (H2O and with Et2O); yield 12.13 g (57%), mp 264°-266° C. MS (EI) m/e 214 (M+), 213 (M-1, base), 169 (M-45), 167 (M-47).

Workup

  1. temperatureAfter cooling
  2. customthe solid that formed
  3. filtrationwas filtered
  4. washwashed with Et2O
  5. customThe solid was triturated with NaHCO3 solution (pH 8)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-761721c1b4e544518a6264f6457fcf3e
Source dataset
uspto-grants-1995_12
Patent number
US05475012

Reaction notes

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