t-Butyl 2-benzylamino-6-methoxypyridine-4-carboxylate → t-Butyl 2-amino-6-methoxypyridine-4-carboxylate

HRID 1612466Notes

Reaction equation

HRID 1612466 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[C:11]([O:22][CH3:23])[N:10]=1)C1C=CC=CC=1>CC(O)=O.[Pd]>[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:12]=[C:11]([O:22][CH3:23])[N:10]=1

Participants

4

Reactant 1

HCID 22253064t-Butyl 2-benzylamino-6-methoxypyridine-4-carboxylate

Product 1

HCID 22252993t-Butyl 2-amino-6-methoxypyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

t-Butyl 2-benzylamino-6-methoxypyridine-4-carboxylate (D54) (0.294 g) in glacial AcOH (50 mL) was hydrogenated for 5 h at atmospheric pressure and room temperature in the presence of Pd—C (10%; 0.25 g). The catalyst was filtered off and washed thoroughly on the filter with MeOH. The combined filtrates were evaporated to give the title compound (D55) as a gum (0.184 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed thoroughly on the
  3. filtrationfilter with MeOH
  4. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-c2d4c1e949224d15b64a25e2e48386f6
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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