Ethyl Acetate → 6-amino-N,N-dimethylpyridine-3-carboxamide

HRID 449590Notes

Reaction equation

HRID 449590 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[CH:6][N:5]=1)=[N+]=[N-].C(OCC)(=O)C>[Pd].CO>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 805835546-azido-N,N-dimethylnicotinamide

Product 1

HCID 575045326-amino-N,N-dimethylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In a 250 mL round-bottomed flask, 6-azido-N,N-dimethylnicotinamide (2.26 g, 11.8 mmol) was combined with ethyl acetate (50 ml) and methanol (30 ml) to give a yellow solution. 10% Pd/C (200 mg, 1.88 mmol) was added and the reaction mixture was evacuated and filled with H2 twice. The reaction mixture was stirred under balloon pressure of H2 at 25° C. for 17 h. The reaction mixture was filtered through celite and the filter cake was washed with MeOH. The filtrate was concentrated in vacuo and the cream colored solid was dried under vacuum at 45° C. for 3 hrs to give the title compound in quantitative yield. (M+H)+=166 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ: 8.21 (d, J=2.3 Hz, 1H), 7.59 (dd, J=8.3, 2.3 Hz, 1H), 6.50 (d, J=8.7 Hz, 1H), 4.69 (br. s., 2H), 3.08 (s, 6H).

Workup

  1. customto give a yellow solution
  2. customthe reaction mixture was evacuated
  3. additionfilled with H2 twice
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe filter cake was washed with MeOH
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe cream colored solid was dried under vacuum at 45° C. for 3 hrs

Sources & evidence

ORD record
ord-1265ef5f0c23482ea7c3dc7b38aa6ad7
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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