Ethanol → HCID 13851042, compound

HRID 986763Notes

Reaction equation

HRID 986763 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:20])[CH2:18][OH:19])=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([O:23]CC)=[O:22].C(O)C.[OH-].[Na+]>O>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:20])[CH2:18][OH:19])=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13851041HCID 13851041, compound

Product 1

HCID 13851042HCID 13851042, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-amino-7-(2-hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate (480 mg), ethanol (40 ml), water (5 ml) and 1N sodium hydroxide (5 ml) was heated at 50° C. for 80 minutes, which was then concentrated. The concentrate was dissolved in water, which was made acid with 10% hydrochloric acid. Resulting precipitates were collected by filtration, washed with water, and recrystallized from dimethylformamide-ethanol-water to yield colorless crystals (386 mg) of 2-amino-7-(2-hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano-[2,3-b]pyridine-3-carboxylic acid, m.p. >300° C.

Workup

  1. concentrationwhich was then concentrated
  2. dissolutionThe concentrate was dissolved in water
  3. customResulting
  4. customprecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customrecrystallized from dimethylformamide-ethanol-water

Sources & evidence

ORD record
ord-5ead4e7b22514ca9be03c4f8252e3c93
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

Loading…