Ammonium formate → HCID 178524346, compound

HRID 606577Notes

Reaction equation

HRID 606577 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[N:13]([CH3:17])C=CN=2)=[CH:6][CH:5]=1.[CH:19]([O-])=O.[NH4+:22]>C(O)(C)C.[Pd]>[NH:22]1[CH:19]=[C:12]([CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:2])=[O:18])=[CH:9][CH:8]=2)[N:13]=[CH:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67046521HCID 67046521, compound

Product 1

HCID 178524346HCID 178524346, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

E-4-[2-(1-Methyl-1H-imidazol-2-yl)-vinyl]-benzoic acid methyl ester was hydrogenated using Pd/C (10% of substrate weight), ammonium formate (5 equivalents) in isopropanol heated by microwave irradiation (200 W) for 5 mins at 150° C. The solution was filtered through celite to remove the insoluble catalyst, diluted with water and freeze-dried to remove the excess of ammonium formate. The obtained solid was hydrolysed by 6N aqueous HCl solution heated by microwave irradiation (200 W) for 3 mins at 150° C. The solution was freeze dried to give to the hydrochloride salt of the title compound as a white powder m/z=217 in MS ES+, which was characterised by HPLC and MS.

Workup

  1. filtrationThe solution was filtered through celite
  2. customto remove the insoluble catalyst
  3. additiondiluted with water
  4. customfreeze-dried
  5. customto remove the excess of ammonium formate
  6. temperatureheated by microwave irradiation (200 W) for 3 mins at 150° C
  7. customdried

Sources & evidence

ORD record
ord-aec95e1571944f33a66f0d15aa2f7bf8
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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