Water → HCID 178482060, compound

HRID 928887Notes

Reaction equation

HRID 928887 reaction equation
[C:1]1([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]=O.O>C(Cl)Cl>[C:20]1([C:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2/[N:9]=[CH:32]/[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 6294252,4,6-Triphenylaniline

Product 1

HCID 178482060HCID 178482060, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In air, to a solution of 2,4,6-triphenylaniline (0.964 g, 3.00 mmol, 1.00 equiv) in CH2Cl2 (10 mL) was added 2-pyridinecarboxaldehyde (0.326 g, 0.290 mL, 3.05 mmol, 1.02 equiv). After heating at reflux for 20 h with azeotropic removal of water using a Dean-Stark trap, the reaction mixture was concentrated under reduced pressure. The residue was purified by trituration with hexanes and dried in vacuo to give the title compound as a yellow solid (1.18 g, 96% yield).

Workup

  1. temperatureAfter heating
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by trituration with hexanes
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c823db0b90304fba8067a0e61cc2fdab
Source dataset
uspto-grants-2016_03
Patent number
US09290591B2

Reaction notes

Loading…