Ammonium formate → HCID 136144409, compound

HRID 1379692Notes

Reaction equation

HRID 1379692 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][CH:32]=[CH:31][CH:30]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO.C(Cl)(Cl)Cl>CCO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][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:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 2723923Ammonium formate2×HCID 18923779HCID 18923779, compoundHCID 21584188Chloroform methanol

Product 1

HCID 136144409HCID 136144409, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The 2-(4-benzyloxyphenyl)-3-(4-methoxyphenyl)-6-phenylpyridine (3.5 g, 7.9 mmol) and ammonium formate (2.5 g, 40 mmol) were stirred in 150 mL of EtOH, then 5% Pd/ C (1.4 g, 0.6 mmol Pd) was added and the reaction mixture was stirred at 60 ° C. for 1 h. The TLC (MeOH/ CHCl3, 1:9) indicated a small amount of the starting material remained, so more ammonium formate (0.3 g, 5 mmol) was added and reaction mixture stirred at 60° C. for 0.5 h, which consumed the remaining starting material. After cooling, the reaction mixture was filtered and the filter pad washed with 50 mL of EtOH, then 50 mL of EtOAc. The filtrates were combined and concentrated, then redissolved in 150 mL of EtOAc, washed with brine, dried (Na2SO4), concentrated, and the residue triturated with Et2O/ pet. ether to give 2.5 g (90% yield) of white solid: mp 200°-202° C.; 1H NMR (CDCl3) d 3.85 (s, 3H, OCH3), 5.07 (s, 1H, ArOH), 6.71-6.90 (m, 4H, ArH), 7.17-7.20 (d, 2H, J=8 Hz, ArH), 7.38-7.54 (m, 5H, ArH), 7.75 (s, 2H, ArH), 8.13-8.16 (d, 2H, J=9 Hz, ArH); MS(FD) 354(M+). Anal. Calcd for C24H19 NO2 : C, 81.56; H, 5.42; N, 3.96. Found: C, 81.50; H, 5.61; N, 3.99.

Workup

  1. customreaction mixture
  2. stirringstirred at 60° C. for 0.5 h
  3. customwhich consumed the
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. washthe filter pad washed with 50 mL of EtOH
  7. concentrationconcentrated
  8. dissolutionredissolved in 150 mL of EtOAc
  9. washwashed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customthe residue triturated with Et2O/ pet. ether

Sources & evidence

ORD record
ord-b35566c8ddbb4278879b5d2c9d1f2296
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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