Ammonia → 1,6-Naphthyridin-2-amine

HRID 1173123Notes

Reaction equation

HRID 1173123 reaction equation
Cl[C:2]1[C:11]2[C:6](=C[C:8]([NH:12]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH3:23]>>[NH2:23][C:8]1[CH:9]=[CH:10][C:11]2[C:6](=[CH:5][CH:4]=[N:3][CH:2]=2)[N:12]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22674092HCID 22674092, compound

Product 1

HCID 5893531,6-Naphthyridin-2-amineYield 89.73%

Procedure

2-Chloro-1,6-naphthyridine (0.628 g, Production Example 22b) and an aqueous ammonia (40 ml) were heated at 130° C. for 11 hours in a sealed tube. After cooling, the mixture was extracted with ethyl acetate, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column, to give the title compound (0.497 g, 89.73%) as pale yellow crystals.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-b492d7e909e84a3b8aeb98ec74f19799
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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