Potassium Hydroxide → HCID 67240458, compound

HRID 335689Notes

Reaction equation

HRID 335689 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[OH-].[K+]>>[Br:1][C:2]1[CH:10]=[C:6]2[C:7](=[O:9])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[O:11][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 58466245HCID 58466245, compound

Product 1

HCID 67240458HCID 67240458, compound

Procedure

A slurry of 5-bromo-2-(4-methoxyphenoxy)nicotinic acid (12.20 g, 37.6 mmol) and polyphosphoric acid (200 g) was heated at 135° C. for 1.5 hours. The reaction was cooled to rt and poured onto 300 g of ice before being basified to pH 12 with 50% aq. KOH (1.5 L). The resulting yellow slurry was filtered and washed with 100 mL of ether. The wet solid was then partitioned between water and DCM (1:1; 2000 mL). The layers were separated and the aqueous layer was extracted with DCM 5×500 mL. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to provide 3-bromo-7-methoxy-5H-chromeno[2,3-b]pyridin-5-one as a yellow solid. MS m/z=306.2 [M+H]+. Calc'd for C13H9BrNO3: 306.0.

Workup

  1. filtrationThe resulting yellow slurry was filtered
  2. washwashed with 100 mL of ether
  3. customThe wet solid was then partitioned between water and DCM (1:1; 2000 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM 5×500 mL
  6. washThe combined organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-536cbe1bfbc04dcbac951aa7a810902f
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…