Ammonium formate → HCID 135493010, compound

HRID 1379691Notes

Reaction equation

HRID 1379691 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]([CH3:29])[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]([CH3:29])[N:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 18923789HCID 18923789, compoundHCID 21584188Chloroform methanol

Product 1

HCID 135493010HCID 135493010, compoundYield 8,905.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

The 2-(4-benzyloxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (14 g, .37 mmol) and ammonium formate (3.5 g, 55 mmol) were stirred in 1 L of EtOH, then 5% Pd/ C (5.8 g, 3 mmol Pd) was added and the reaction mixture warmed to 50°-55° C. The reaction mixture was stirred at 55° C. for 1 h at which time the TLC (MeOH/ CHCl3, 1:9) indicated the starting material was consumed. After cooling, the reaction mixture was filtered, concentrated, and the residue triturated with Et2O to give 9.6 g (90% yield) of white solid: mp 190° C.; 1H NMR (CDCl3) d 2.66 (s, 3H, Pyr-CH3), 3.82 (s, 3H, OCH3), 6.53-6.56 (d, 2H, J=8 Hz, ArH), 6.80-6.83 (d, 2H, J=8 Hz, ArH), 7.06-7.18 (m, 6H, ArH, ArOH), 7.59-7.62 (d, 1H, J=8 Hz, ArH); MS(FD) 291(M+). Anal. Calcd for C19H17NO2 : C, 78.33; H, 5.88; N, 4.81. Found: C, 78.11; H, 5.93; N, 4.72.

Workup

  1. temperaturethe reaction mixture warmed to 50°-55° C
  2. customwas consumed
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated
  6. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-00fecb449f664609a5157a622ae65cb8
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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