Ammonium formate → HCID 69455593, compound

HRID 1293429Notes

Reaction equation

HRID 1293429 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)(C)C.[Pd]>[NH2:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69455591HCID 69455591, compound

Product 1

HCID 69455593HCID 69455593, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4′-cyano-4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-carbamic acid benzyl ester (240 mg), ammonium formate (300 mg), and Pd/C (20 mg) in isopropyl alcohol (8 mL) was heated at 80° C. for 30 min. The reaction mixture was cooled and filtered through diatomaceous earth to provide 4-amino-4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carbonitrile (150 mg) as a foam. MS (CI) m/z 217 (M+H)+; 1H NMR (300 MHz, MeOH-d4) δ 8.54 (s, 1H), 8.06 (d, 1H), 6.89 (d, 1H), 4.02-3.85 (m, 2H), 3.40-3.32 (m, 2H), 1.81-1.78 (m, 4H), 1.35 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through diatomaceous earth

Sources & evidence

ORD record
ord-0f2205c1bb6b4eacacd13ba4267bc1e6
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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