Sodium Hydroxide → HCID 20156362, compound

HRID 986761Notes

Reaction equation

HRID 986761 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([O:23]CC)=[O:22].[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([C:17]([OH:20])([CH3:18])[CH3:19])=[CH:13][C:10]=3[C:11](=[O:12])[C:5]2=[CH:4][C:3]=1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15598959HCID 15598959, compound

Product 1

HCID 20156362HCID 20156362, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension consisting of ethyl 2-amino-7-(1-hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]-pyridine-3-carboxylate (37.3 g), ethanol (2.3 l) and 0.5N sodium hydroxide (620 ml) was stirred at 50° C. for 2 hours, then ethancl was evaporated off. The concentrate was acidified with hydrochloric acid (pH 3-4), then the resulting precipitates were collected by filtration and washed with water, followed by recrystallization from dimethylformamide-water. The crystals were washed with ethanol to give 2-amino-7-(1-hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]-pyridine-3-carboxylic acid (32.5 g).

Workup

  1. customwas evaporated off
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customfollowed by recrystallization from dimethylformamide-water
  6. washThe crystals were washed with ethanol

Sources & evidence

ORD record
ord-13ac5640ecb64969a10f6e4d255a1cd1
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

Loading…