Pyridine → HCID 22218265, compound

HRID 1166691Notes

Reaction equation

HRID 1166691 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:13])[CH:5]=[CH:4][C:3]1=2.[C:15](Cl)(=[O:17])[CH3:16].N1C=CC=CC=1>ClCCl.Cl>[CH3:1][C:2]1([CH3:14])[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]2[CH:7]=[C:6]([NH:13][C:15](=[O:17])[CH3:16])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22218301HCID 22218301, compound2×

Product 1

HCID 22218265HCID 22218265, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

General Procedure T A solution of 5,5,8-trimethyl-5,6-dihydro-naphthalen-2-ylamine (Compound 159, 1.47g, 7.9 mmol) in 10 mL of dichloromethane was stirred at 0° C., and acetyl chloride (1.0 mL, 1.39 g, 18 mmol) and then pyridine (1.0 mL, 1.0 g, 12 mmol) were added, and the reaction stirred at 0° C. for 1 h. The reaction mixture was then diluted with 10% HCl and extracted two times with methylene chloride. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvents were removed in vacuo. The residual crude product was purified by silica gel chromatography (30% ethyl acetate in hexanes) to give the title compound as a white solid, which was immediately used in the next step.

Workup

  1. extractionextracted two times with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customThe residual crude product was purified by silica gel chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-51d1ba66d33746aca6035231ded0a804
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

Loading…