Sodium hydroxide--water (1/1/1) → HCID 178524532, compound

HRID 2073333Notes

Reaction equation

HRID 2073333 reaction equation
[OH-].[Na+].O.[CH:4]1([NH:7][C:8]2[N:18]=[C:17]([OH:19])[C:16]([F:20])=[CH:15][C:9]=2[C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1>C(O)C>[CH:4]1([NH:7][C:8]2[N:18]=[C:17]([OH:19])[C:16]([F:20])=[CH:15][C:9]=2[C:10]([OH:12])=[O:11])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 23719242Sodium hydroxide--water (1/1/1)HCID 178469123HCID 178469123, compound

Product 1

HCID 178524532HCID 178524532, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 95% ethanol (20 ml) and 2N NaOH/H2O (40 ml) was added 2.65 g of ethyl 2-cyclopropylamino-5-fluoro-6-hydroxynicotinate. The inital suspension was refluxed for a total of six hours, then cooled, and evaporated to a solid. The solid was dissolved in 30 ml of H2O and acidified to pH=1 with 2N HCl solution. The solid formed upon acidification was collected by filtration and washed with H2O to give the crude acid product. This product was triturated with hot 95% ethanol, filtered, and dried to give 1.65 g of a beige colored solid, 2-cyclopropyl-5-amino-6-hydroxynicotinic acid.

Workup

  1. temperatureThe inital suspension was refluxed for a total of six hours
  2. temperaturecooled
  3. customevaporated to a solid
  4. dissolutionThe solid was dissolved in 30 ml of H2O
  5. customThe solid formed upon acidification
  6. filtrationwas collected by filtration
  7. washwashed with H2O
  8. customto give the crude acid product
  9. customThis product was triturated with hot 95% ethanol
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-82205beaab9545f6b69839c4c1cd323e
Source dataset
uspto-grants-1990_04
Patent number
US04916229

Reaction notes

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