Methanol → 3-Amino-5-bromopyridine-2-carboxamide

HRID 873315Notes

Reaction equation

HRID 873315 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[C:9]([N+:15]([O-])=O)[C:10]([C:13]#[N:14])=[N:11][CH:12]=1.C[OH:19]>>[NH2:15][C:9]1[C:10]([C:13]([NH2:14])=[O:19])=[N:11][CH:12]=[C:7]([Br:6])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24287Tin tetrachlorideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 210758623-Amino-5-bromopyridine-2-carboxamide

Conditions

Temperature
40 °C

Procedure

Tin chloride (90 g, 400 mmol) was added to a solution of 5-bromo-3-nitropicolinonitrile (17 g, 74 mmol) in methanol (800 mL) and the reaction was heated to 40° C. for 4.75 h. The solvent was removed in vacuo and toluene added and removed in vacuo. The crude was suspended in EtOAc and the mixture basified to pH 8 with saturated NaHCO3 (aq). The organic layer was separated and the aqueous slurry extracted with CHCl3 (×3). The combined organics were filtered through Celite, dried (MgSO4) and concentrated in vacuo to give crude 3-amino-5-bromopyridine-2-carboxamide which was used directly without further purification.

Workup

  1. customThe solvent was removed in vacuo and toluene
  2. additionadded
  3. customremoved in vacuo
  4. customThe organic layer was separated
  5. extractionthe aqueous slurry extracted with CHCl3 (×3)
  6. filtrationThe combined organics were filtered through Celite
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7ea92e4968946309ec3b43a930bc251
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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