Ethyl Acetate → HCID 136207703, compound

HRID 1379694Notes

Reaction equation

HRID 1379694 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+].CCOC(C)=O>CCO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[N:16]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formate2×HCID 18923794HCID 18923794, compound

Product 1

HCID 136207703HCID 136207703, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 2-(4-benzyloxyphenyl)-3,6-bis(4-methoxyphenyl)pyridine (3.0 g, 6.3 mmol), ammonium formate (2.0 g, 31 mmol), and 5% Pd/C (1.0 g, 0.5 mmol Pd) were combined in 150 mL of EtOH, and the reaction mixture was stirred at 50°-55 ° C. and followed by TLC (EtOAc/ Tol, 1:9). After 1 h, more ammonium formate (0.5 g, 8 mmol) was added and reaction mixture stirred at 50° C. for 30 min and no starting material remained. After cooling, the reaction mixture was filtered, concentrated, and the residue triturated with Et2O/ pet. ether. The white ppt was filtered and dried in vacuo to give 2.35g (97% yield) of product: mp 204°-205° C.; 1H NMR (CDCl3) d 3.83 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 4.85 (s, 1H, ArOH), 6.71-6.74 (d, 2H, J=9 Hz, ArH), 6.83-6.86 (d, 2H, J=9 Hz, ArH), 7.00-7.03 (d, 2H, J=9 Hz, ArH), 7.14-7.17 (d, 2H, J=9 Hz, ArH), 7.37-7.40 (d, 2H, J=9 Hz, ArH), 7.68-7.70 (m, 2H, ArH), 8.08-8.11 (d, 2H, J=9 Hz, ArH); MS(FD) 383(M+). Anal. Calcd for C25H21NO3 : C, 78.31; H, 5.52; N, 3.65. Found: C, 78.07; H, 5.79; N, 3.95.

Workup

  1. customreaction mixture
  2. stirringstirred at 50° C. for 30 min
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated
  6. customthe residue triturated with Et2O/ pet. ether
  7. filtrationThe white ppt was filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-dc7e6d7cbbba473bb614df05fb2ac2bb
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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