2-Aminopyridine → 56000-35-2

HRID 1621169Notes

Reaction equation

HRID 1621169 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]>ClCCl>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 1226419056000-35-2Yield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of O-(mesitylsulfonyl)hydroxylamine (9.2 g, 42.7 mmol) in dichloromethane (110 mL) was added pyridin-2-amine (4.02 g, 42.7 mmol) in four portions at 0-5° C. to give a yellow solution. After 5 min the yellow solution turned into a light yellow suspension. The ice bath was removed after 10 min and the reaction mixture was stirred at RT for 1 h. The suspension was diluted with diethyl ether (100 mL), filtered, washed with diethyl ether and dried in vacuo to give the product (10.9 g, 35.2 mmol, 82.4%) as light red solid which was used without further purification for the next step.

Workup

  1. customto give a yellow solution
  2. customThe ice bath was removed after 10 min
  3. additionThe suspension was diluted with diethyl ether (100 mL)
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-43e33c7c78274cb99f3f8b054f19d093
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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