Tetrahydrofuran → HCID 178431739, compound

HRID 234291Notes

Reaction equation

HRID 234291 reaction equation
[OH-:1].[K+].[N:3]1([CH2:14][CH2:15][C:16](N)=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=O)[C:4]1=[O:5].C1C[O:22]CC1>>[OH:1][C:14]1[C:15]([CH3:16])=[C:6]([C:4]([OH:22])=[O:5])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14797Potassium HydroxideHCID 43131892HCID 43131892, compound

Product 1

HCID 178431739HCID 178431739, compound

Procedure

Potassium hydroxide (1N, 100.0 ml) is added to a mixture of 5-fluoroisatin acetamide (IV, 8.44 g) and THF (33 ml). The mixture is heated at reflux for 1 hr, allowing the THF to distill off. The mixture is then cooled to 5° and is extracted with methylene chloride (3×50 ml). The basic layer is neutralized with hydrochloric acid (4N, 16.3 ml) and the resulting solids collected and washed with water (200 ml) and methylene chloride (100 ml) to give 6-fluoro-2-hydroxyquinoline-4-carboxylic acid (V), mp >293°; IR (mineral oil) 1714, 1648, 1623, 1508, 1436, 1261, 1255, 1244, 1234 and 1222 cm-1 ; NMR (d6 -DMSO) 12.20, 8.04, 7.35-7.60 and 7.00 δ; MS (El, m/e) 207, 162, 135 and 107.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 hr
  3. distillationto distill off
  4. temperatureThe mixture is then cooled to 5°
  5. extractionis extracted with methylene chloride (3×50 ml)
  6. customthe resulting solids collected
  7. washwashed with water (200 ml) and methylene chloride (100 ml)

Sources & evidence

ORD record
ord-6f8d64db2b96466a9abf4d992743bae8
Source dataset
uspto-grants-1997_01
Patent number
US05594140

Reaction notes

Loading…