Morpholine → HCID 66664773, compound

HRID 595836Notes

Reaction equation

HRID 595836 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>>[O:15]1[CH2:16][CH2:17][N:12]([C:2]2[CH:3]=[C:4]([NH2:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 589057095-Bromo-2-nitropyridin-3-amine

Product 1

HCID 66664773HCID 66664773, compoundYield 84.2%

Conditions

Temperature
140 °C

Procedure

5-Bromo-2-nitropyridin-3-amine (2.32 g, 10.6 mmol) was suspended in morpholine (5 mL, 57.4 mmol) and the solution was heated at 140° C. for 1h. The reaction mixture was cooled to room temperature and the solid crash out was triturated with water and filtered. The solid this obtained was washed with water, EtOH, and dried, obtaining 5-morpholino-2-nitropyridin-3-amine (2.0 g, 8.92 mmol, 84%) as a bright yellow powder. Depending on the outcome of the previous step, this solid may still contain the ethoxy derivative from the previous step, and the two compounds can be separated by column chromatography on silica gel (analogix, 20% EtOAc in heptane for 2 min, to 100% EtOAc to 15 min, then 100% EtOAc to 20 min). LCMS (m/z): 225.1 (MH+), 0.43 min; 1H NMR (400 MHz, CDCl3) δ ppm 10.54 (s, 1H) 8.57 (d, J=2.7 Hz, 1H) 7.85 (d, J=2.7 Hz, 1H) 7.70 (d, J=2.3 Hz, 1H) 6.32 (d, J=2.3 Hz, 1H) 6.00 (br. s., 1H) 3.93-3.83 (m, 7H) 3.83-3.74 (m, 3H) 3.63-3.55 (m, 3H) 3.51-3.43 (m, 3H) 3.41-3.31 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solid crash out was triturated with water
  3. filtrationfiltered
  4. washThe solid this obtained was washed with water, EtOH
  5. customdried

Sources & evidence

ORD record
ord-3c5a199cbdf54686a3d002c3a745b3f8
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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