Ammonia methanol → HCID 178428521, compound

HRID 1501262Notes

Reaction equation

HRID 1501262 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([OH:10])[N:5]=[C:4]([CH3:11])[CH:3]=1.CO.[NH3:14]>>[NH2:14][C:2]1[C:7]([C:8]#[N:9])=[C:6]([OH:10])[N:5]=[C:4]([CH3:11])[CH:3]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 178426119HCID 178426119, compound

Product 1

HCID 178428521HCID 178428521, compoundYield 66%

Conditions

Temperature
100 °C

Procedure

To a pressure vessel were added 4-chloro-2-hydroxy-6-methylnicotinonitrile (600 mg, 3.6 mmol), ammonia methanol solution (7 mol/L, 15 mL) and magnetic stirrer. The pressure vessel was sealed, and stirred at 100° C. for 16 hours. After being cooled to room temperature, the solvent and excess ammonia were removed by rotary evaporation. The residue was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 4-amino-2-hydroxy-6-methylnicotinonitrile (350 mg, 66% yield) as a brown solid.

Workup

  1. customThe pressure vessel was sealed
  2. temperatureAfter being cooled to room temperature
  3. customthe solvent and excess ammonia were removed by rotary evaporation
  4. customThe residue was purified by silica gel column chromatography with dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-5f113701952146679c936ed9ee72a28b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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