Methylamine tetrahydrofuran → HCID 178482200, compound

HRID 1501268Notes

Reaction equation

HRID 1501268 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.O1CCCC1.[CH3:17][NH2:18]>>[OH:10][C:6]1[N:5]=[C:4]([CH3:11])[CH:3]=[C:2]([NH:18][CH3:17])[C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 66615946Methylamine tetrahydrofuranHCID 178426119HCID 178426119, compound

Product 1

HCID 178482200HCID 178482200, compoundYield 61%

Conditions

Temperature
90 °C

Procedure

To a pressure vessel were added 4-chloro-2-hydroxy-6-methylnicotinonitrile (337 mg, 2.0 mmol), methylamine tetrahydrofuran solution (2 mol/L, 15 mL), and magnetic stirrer. The pressure vessel was sealed, and it was stirred at 90° C. for 2 hours. After being cooled to room temperature, the vessel was opened, and the reaction solution was transferred to an eggplant-shaped bottle. The solvent and excess methylamine were removed by rotary evaporation. The residue was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 2-hydroxy-6-methyl-4-(methylamino)nicotinonitrile (200 mg, 61% yield) as a brown solid. 1H NMR (300 MHz, methanol-d4): δ 5.89 (s, 1H), 3.56 (d, J=10.8 Hz, 3H), 2.94 (s, 1H), 2.55 (s, 1H), 2.24 (s, 1H).

Workup

  1. customThe pressure vessel was sealed
  2. temperatureAfter being cooled to room temperature
  3. customThe solvent and excess methylamine 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-4e2fa91fce464eee96c7c82e2ac2fbc0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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