Acetic Acid → HCID 53856658, compound

HRID 974782Notes

Reaction equation

HRID 974782 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.N1CCCCC1.C(O)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[CH:20][C:17]1[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=1)[C:8]2=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 133894-PyridinecarboxaldehydeHCID 366205-Methoxytetralone

Product 1

HCID 53856658HCID 53856658, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-methoxy-1-tetralone (0.1 g; 0.56 mmol), pyridine-4-carboxaldehyde (91 μl ; 0.85 mmol), piperidine (16.8 μl; 0.17 mmol) and acetic acid (9.7μl ; 0.17 mmol) was heated at 130° C. for one hour. The mixture was taken up in CH2Cl2 and washed in water and in a saturated aqueous solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with CH2Cl2 /CH3CN (7/3) to give 5-methoxy-2-(4-pyridylmethylene)-1-tetralone (74 mg; 52%).

Workup

  1. washwashed in water and in a saturated aqueous solution of NaCl
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with CH2Cl2 /CH3CN (7/3)

Sources & evidence

ORD record
ord-58075ec51ed446479de196390fbacb13
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

Loading…