Ammonia → 1279815-28-9

HRID 1050347Notes

Reaction equation

HRID 1050347 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]([NH2:11])=[O:10].[NH3:12]>O1CCOCC1>[NH2:12][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 6000444,6-Dichloronicotinamide

Product 1

HCID 1185985571279815-28-9

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a well stirred solution of 4,6-dichloropyridine-3-carboxamide (11.0 g, 57.59 mmol) in 1,4-dioxane (20 mL) in steel bomb was added the liquid ammonia (50 mL, 57.59 mmol). The steel bomb was closed and heated the reaction to 100° C. for 9 h. The progress of the displacement reaction was monitored by TLC and LCMS. After completion the solid formed was filtered. The filtrate was also concentrated as it also contains 50% product. The combined solids were dried under vacuum to afford 4-amino-6-chloro-pyridine-3-carboxamide (2) as a light brown solid. Yield: 10.6 g, crude, 47%; 1H NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 7.97 (s, 1H), 7.50 (s, 1H), 7.37 (s, 1H), 6.65 (s, 1H).

Workup

  1. temperatureheated
  2. customthe reaction to 100° C. for 9 h
  3. customThe progress of the displacement reaction
  4. customAfter completion the solid formed
  5. filtrationwas filtered
  6. concentrationThe filtrate was also concentrated as it also contains 50% product
  7. customThe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-29bf2b56551a4d088895cfde1c9247ad
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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