Ethanol → 3-Amino-6-chloropyridine-2-carboxamide

HRID 1485538Notes

Reaction equation

HRID 1485538 reaction equation
Cl[Sn]Cl.[Cl:4][C:5]1[N:10]=[C:9]([C:11]#[N:12])[C:8]([N+:13]([O-])=O)=[CH:7][CH:6]=1.CC[OH:18]>>[NH2:13][C:8]1[C:9]([C:11]([NH2:12])=[O:18])=[N:10][C:5]([Cl:4])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24479Stannous ChlorideHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 107497043-Amino-6-chloropyridine-2-carboxamideYield 96%

Conditions

Temperature
90 °C

Procedure

SnCl2 (27.5 g, 122 mmol) was added to a suspension of 6-chloro-3-nitropicolinonitrile (5.60 g, 30.5 mmol) in EtOH (40 mL) at room temperature. The reaction mixture was heated at 90° C. for 2 h. After cooled to room temperature, the solvent was removed under reduced pressure, EtOAc was poured into the residue. The mixture was neutralized with aq. Na2HCO3 and aq. NaOH until pH ˜9, filtered through a Celite pad. The filtrate was extracted with EtOAc, dried over Na2SO4, and concentrated in vacuo to give 3-amino-6-chloropicolinamide (5.00 g, 96%) as a yellow solid which was used for the next step without further purification. 1H-NMR (DMSO-d6, Varian 400 MHz) δ 7.01 (2H, brs), 7.22 (1H, d, J=8.8 Hz), 7.30 (1H, d, J=8.8 Hz), 7.42 (1H, brs), 7.71 (1H, brs). m/z=171.98 [M+1]+.

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was removed under reduced pressure, EtOAc
  3. additionwas poured into the residue
  4. filtrationfiltered through a Celite pad
  5. extractionThe filtrate was extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9627aab52d8472c8790730d49f90545
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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