Ammonium formate → HCID 66777797, compound

HRID 878470Notes

Reaction equation

HRID 878470 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:5]=1[NH:16][C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:5]=1[NH:16][C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 45258643HCID 45258643, compound

Product 1

HCID 66777797HCID 66777797, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate (270 mg, 0.70 mmol) and ammonium formate (177 mg, 2.8 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give methyl 8-(4-aminobiphenyl-3-ylamino)-8-oxooctanoate (211 mg)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-d7564d3812854df68a1881a65fcc04f3
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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