Ethyl 2-methyl-5-nitronicotinate → Ethyl 5-amino-2-methylnicotinate

HRID 2065568Notes

Reaction equation

HRID 2065568 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[N:7][C:6]=1[CH3:14])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[N:7][C:6]=1[CH3:14])[CH3:2]

Participants

4

Reactant 1

HCID 287239Ethyl 2-methyl-5-nitronicotinate

Product 1

HCID 22180329Ethyl 5-amino-2-methylnicotinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-nitro-nicotinic acid ethyl ester 7 (1.43 mmol) in MeOH (15 mL) is added Pd (5% on carbon, 50% wet; 10% weight). After purging, the reaction mixture is stirred under hydrogen atmosphere for 3 h. The solvent is filtered through celite and the celite cake is washed with MeOH. The solvent is removed under vacuum to afford 5-amino-2-methyl-nicotinic acid ethyl ester 8 as yellow solid, which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 7.19 (d, J=4.0 Hz, 1H), 6.78 (d, J=4.0 Hz, 2H), 4.10 (s, 2H), 3.56 (q, J=8.0 Hz, 2H), 1.80 (s, 3H), 0.59 (t, J=8.0 Hz, 3H). MS (m/z) (M+1)+: 182.0.

Workup

  1. customAfter purging
  2. filtrationThe solvent is filtered through celite
  3. washthe celite cake is washed with MeOH
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-171eb51be882404c9b2eb9da159de1e1
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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