5-Phenyl-2-pyridinamine → HCID 24995120, compound

HRID 655992Notes

Reaction equation

HRID 655992 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][N:11]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 1050975-Phenyl-2-pyridinamineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 24995120HCID 24995120, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-phenylpyridin-2-amine (340 mg, 2 mmol) in 10 mL of dry pyridine was added 3,4-dimethoxybenzenesulfonyl chloride (529 mg, 2.23 mmol). The solution was stirred at room temperature under Argon. After 19 h, the pyridine was removed in vacuo and flashed off with toluene, the solid residue was partitioned between EtOAc and 1M NaOH. The alkaline phase was made acidic and the solid was collected by filtration and dried in vacuo to give 511 mg of a solid. This was taken up in 5 mL of HOAc, diluted with 3 mL of water; crystallization took place to give 447 mg of a white crystalline product with mp 202-204° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customthe solid residue was partitioned between EtOAc and 1M NaOH
  3. filtrationthe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3cf22e4b5e234afca1ed9a2a6b259c18
Source dataset
uspto-grants-2011_12
Patent number
US08071631B2

Reaction notes

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