3-Nitropicolinaldehyde → 3-Aminopyridine-2-carbaldehyde

HRID 473434

Reaction equation

HRID 473434 reaction equation
[N+:1]([C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 3293613-Nitropicolinaldehyde

Product 1

HCID 122040093-Aminopyridine-2-carbaldehydeYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-nitropicolinaldehyde (500 mg, 3.28 mmol) in EtOH (10 mL) was added Pd/C (50 mg) under nitrogen atmosphere. The reaction mixture was stirred for overnight under hydrogen atmosphere. The reaction mixture was filtered through cilite and washed with EtOH. The filtrate was concentrated in vacuo to give 3-aminopicolinaldehyde (200 mg, 50% yield): 1H NMR (400 MHz, DMSO-d6) δ 7.132 (br s, 2H), 7.217-7.325 (m, 2H), 7.979 (dd, J=1.6 Hz, J=4.0 Hz, 1H), 9.899 (s, 1H); LC-MS (ESI) m/z 123.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through cilite
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7bc10bd860ce42e69d3338afce772368
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Linked notes

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