Hydrochloric Acid → HCID 13728612, compound

HRID 986762Notes

Reaction equation

HRID 986762 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:22][C:11]3=[N:12][C:13]([NH2:21])=[C:14]([C:16]([O:18]CC)=[O:17])[CH:15]=[C:10]3[C:9](=[O:23])[C:8]=2[CH:24]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:22][C:11]3=[N:12][C:13]([NH2:21])=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=[C:10]3[C:9](=[O:23])[C:8]=2[CH:24]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13728611HCID 13728611, compound

Product 1

HCID 13728612HCID 13728612, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In ethanol (3 l) was suspended ethyl 7-acetyl-2-amino-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate (46 g). To the suspension were added water (460 ml) and 1N sodium hydroxide (462 ml). The mixture was stirred at room temperature for 1.5 hour, then at 50°-55° C. for 2 hours. The precipitating crystals were collected by filtration, and washed with ethanol. The crystals thus obtained were suspended in warm water (about 2 l). To the suspension was added concentrated hydrochloric acid (20 ml), and the mixture was stirred for 20 minutes. Insoluble matter was collected by filtration, washed with water, followed by recrystallization from dimethylformamide-water to give 7-acetyl-2-amino-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid as colorless crystals (39.3 g). Melting point: >300° C.

Workup

  1. waitat 50°-55° C. for 2 hours
  2. filtrationThe precipitating crystals were collected by filtration
  3. washwashed with ethanol
  4. customThe crystals thus obtained
  5. stirringthe mixture was stirred for 20 minutes
  6. filtrationInsoluble matter was collected by filtration
  7. washwashed with water
  8. customfollowed by recrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-e315e9a42d544c98937e7404ad3dcafe
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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