Water → HCID 14390458, compound

HRID 622956Notes

Reaction equation

HRID 622956 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[O:17][C:18]([Br:21])=[CH:19][CH:20]=2)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)C.O.[OH-].[K+]>C(O)CO.CO>[Br:21][C:18]1[O:17][C:16]([C:14]2[N:6]([CH2:5][C:4]([OH:3])=[O:22])[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:13]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 14390506HCID 14390506, compound

Product 1

HCID 14390458HCID 14390458, compoundYield 1.6%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

A solution of N-[3-[(5-bromo-2-furanylcarbonyl)amino]-2-pyridinyl]glycine ethyl ester (110 g, 0.30 mole) in ethylene glycol (510 ml) was refluxed under nitrogen for two hours. The solution was cooled to room temperature and water (100 ml) and potassium hydroxide pellets (23.25 g, 0.41 mole) were added. The solution was refluxed for an additional 1.5 hours and then filtered, while hot, into ice water (2 liters). A 3N hydrochloric acid solution was added until the suspension was acidic. After stirring overnight, the solid was collected by filtration and rinsed with water. Most of the wet material was dried at 56° C. overnight under high vacuum to give 79.5 g of crude material (82% yield). A portion (3.0 g of wet material) was dissolved in hot methanol, filtered, and cooled to room temperature. Addition of water caused a solid to precipitate which was collected by filtration, rinsed with water, and dried at high vacuum at 56° C. to give 1.59 g of title compound, mp 229°-231° C.

Workup

  1. temperatureThe solution was refluxed for an additional 1.5 hours
  2. filtrationfiltered
  3. additionA 3N hydrochloric acid solution was added until the suspension
  4. filtrationthe solid was collected by filtration
  5. washrinsed with water
  6. customMost of the wet material was dried at 56° C. overnight under high vacuum
  7. customto give 79.5 g of crude material (82% yield)
  8. filtrationfiltered
  9. temperaturecooled to room temperature
  10. additionAddition of water
  11. customto precipitate which
  12. filtrationwas collected by filtration
  13. washrinsed with water
  14. customdried at high vacuum at 56° C.

Sources & evidence

ORD record
ord-6ba6d0cd7f084dbea4c545c715f6bf9a
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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