Methanol → HCID 86597615, compound

HRID 1725369Notes

Reaction equation

HRID 1725369 reaction equation
[Br:1][N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[O:9]1C2N=CCC(=O)[C:12]=2[CH:11]=[CH:10]1.CO>C(#N)C>[Br:1][N:2]1[C:6]2[O:8][CH:3]=[CH:4][C:5]=2[C:10](=[O:9])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 68886786HCID 68886786, compound

Product 1

HCID 86597615HCID 86597615, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Add N-bromosuccinimide (63.16 g, 354.9 mmol) as a solution in anhydrous acetonitrile (480 mL) to a suspension of 5H-furo[3,2]pyridin-4-one (36.9 g, 273 mmol) in anhydrous acetonitrile (740 mL) at 0° C. over 1 hour. Warm to room temperature, add anhydrous methyl alcohol (1.5 L) and stir at room temperature for 18 hours. Quench with water (20 ml) and saturated sodium bicarbonate (20 mL), concentrate to a volume of 1.3 liters, and pour into water (1.3 L). Collection of the precipitate by filtration and drying (vacuum oven 2 days 40-60° C.) gives the title compound as an off-white solid.

Workup

  1. customQuench with water (20 ml) and saturated sodium bicarbonate (20 mL)
  2. concentrationconcentrate to a volume of 1.3 liters
  3. additionpour into water (1.3 L)
  4. customCollection of the precipitate
  5. filtrationby filtration
  6. customdrying (vacuum oven 2 days 40-60° C.)

Sources & evidence

ORD record
ord-9f218756499f463894b78738114bbd0e
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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