Ammonium formate → Methyl 4'-(2-aminoethyl)-2-methyl-1,1'-biphenyl-4-carboxylate

HRID 1866159Notes

Reaction equation

HRID 1866159 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:21]=2[CH3:30])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[NH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:21]=2[CH3:30])=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22171258Methyl 4'-[2-[[(benzyloxy)carbonyl]amino]ethyl]-2-methyl-1,1'-biphenyl-4-carboxylate

Product 1

HCID 22171624Methyl 4'-(2-aminoethyl)-2-methyl-1,1'-biphenyl-4-carboxylateYield 87.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 4′-[2-[[(benzyloxy)carbonyl]-amino]ethyl]-2-methyl-1,1′-biphenyl-4-carboxylate (650 mg), ammonium formate (500 mg) and palladium on carbon powder (400 mg) in methanol (10 ml) and water (1.0 ml) was refluxed for 2 hours. The reaction mixture was filtrated and poured into water and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and evaporated to give methyl 4′-(2-aminoethyl)-2-methyl-1,1′-biphenyl-4-carboxylate (380 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe reaction mixture was filtrated
  3. additionpoured into water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-dcd2adcbed0145079a053cf02a0a5a6f
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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