Ammonium formate → HCID 9954116, compound

HRID 502037Notes

Reaction equation

HRID 502037 reaction equation
C([O-])=O.[NH4+].[C:5]1([CH2:11][CH2:12][NH:13][C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=1>[Pd].CO>[CH:5]1([CH2:11][CH2:12][NH:13][C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57277554HCID 57277554, compound

Product 1

HCID 9954116HCID 9954116, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (0.224 g) was added to a stirred mixture of 10% palladium-on-carbon (0.015 g), N-(2-cyclohexen-1-ylethyl)-3-(3,4-dimethoxybenzamido)-4-methylbenzamide (0.15 g) and methanol (15 ml) and the reaction mixture was heated to reflux for 1.25 hours. The reaction mixture was allowed to cool and was filtered through diatomaceous earth. The filtrate was evaporated and the residue was triturated under water. The solid so obtained was dried under vacuum at 55° C. to give the title compound as a powder (0.136 g); NMR Spectrum: (CDCl3) 0.8-2.3 (m, 13H), 2.37 (s, 3H), 3.45 (m, 2H), 3.96 (m, 6H), 6.12 (m, 1H), 6.93 (d, 1H), 7.26 (m, 1H), 7.46 (d, 1H), 7.56 (m, 2H), 7.92 (s, 1H), 8.16 (s, 1H); Mass Spectrum: M+H+ 425.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1.25 hours
  3. temperatureto cool
  4. filtrationwas filtered through diatomaceous earth
  5. customThe filtrate was evaporated
  6. customthe residue was triturated under water
  7. customThe solid so obtained
  8. customwas dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-3893e0e6046c40c09b9dece9468c097e
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

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