Methanol → HCID 15233058, compound

HRID 1770324Notes

Reaction equation

HRID 1770324 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][C:13]#[N:14])[N:6]=1)(=[O:3])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].CO>O.N>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16])[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 20096011HCID 20096011, compound

Product 1

HCID 15233058HCID 15233058, compound

Reagents, catalysts & solvents 1

HCID 12896473Azane;hydrateSolvent

Procedure

2-Acetylamino-6-(2-cyanoethyl)pyridine (11.5 mg, 78 μmol) was dissolved in 25% ammonia water (3.0 ml) and, after purging with nitrogen, palladium black (30 mg) was added thereto. After repurging with nitrogen, the mixture was stirred at room temperature under a hydrogen stream at 9 atmospheres for 28 hours. After nitrogen purging, the palladium black was filtered off and the filtrate was concentrated under reduced pressure. Chloroform (500 μl) was added to the residue and, the mixture was cooled with ice and, after addition of acetic anhydride (100 μl, 1.1 mmol), stirred for 10 minutes. After allowing the temperature to rise to room temperature, stirring was continued for 5 hours. After cooling with ice, methanol (1.0 ml) was added and the mixture was stirred for 1 hour and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [silica gel 10 g, chloroform-methanol (19:1)→(15:1)] to give 2-acetylamino-6-(3 -acetylaminopropyl)pyridine as a colorless solid (Yield 6 mg (51%)).

Workup

  1. customafter purging with nitrogen, palladium black (30 mg)
  2. additionwas added
  3. filtrationAfter nitrogen purging, the palladium black was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionChloroform (500 μl) was added to the residue
  6. temperaturethe mixture was cooled with ice
  7. stirringstirred for 10 minutes
  8. customto rise to room temperature
  9. stirringstirring
  10. waitwas continued for 5 hours
  11. additionwas added
  12. stirringthe mixture was stirred for 1 hour
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography [silica gel 10 g, chloroform-methanol (19:1)→(15:1)]

Sources & evidence

ORD record
ord-7c9f792954e045a4b5a4235c7ac96327
Source dataset
uspto-grants-1995_01
Patent number
US05386033

Reaction notes

Loading…