Hydrochloric Acid → HCID 178431739, compound

HRID 1585158Notes

Reaction equation

HRID 1585158 reaction equation
[N:1]1([CH2:12][CH2:13][C:14](N)=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-:17].[K+].Cl.C1C[O:23]CC1>>[OH:17][C:12]1[C:13]([CH3:14])=[C:4]([C:2]([OH:23])=[O:3])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 14797Potassium HydroxideHCID 43131892HCID 43131892, compound

Product 1

HCID 178431739HCID 178431739, compound

Procedure

A mixture of 5-chloroisatin acetamide (IV, 5.00 g), potassium hydroxide (1 N, 56 ml) and THF (18 ml) is heated at reflux for 1 hr, allowing the THF to boil off, and is allowed to cool to 20-25°. The basic mixture is cooled to 0° and acidified to pH 5.5 (pH paper) with hydrochloric acid (4 N). The resulting solids are filtered, washed with water and methylene chloride, dried, and triturated overnight in methylene chloride (200 ml, to remove a small amount of 5-chloroisatin byproduct). These solids are filtered, washed with methylene chloride, and dried to give 6-chloro-2-hydroxyquinoline-4-carboxylic acid (V), mp >3000; IR (mineral oil) 1711, 1645, 1430, 1221, 1179, 887 and 881 cm-1 ; NMR (d6 -DMSO) 12.25, 8.30, 7.62, 7.38 and 7.00 δ; MS (EI, m/e) 223, 178 and 151.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hr
  3. temperatureto cool to 20-25°
  4. temperatureThe basic mixture is cooled to 0°
  5. filtrationThe resulting solids are filtered
  6. washwashed with water and methylene chloride
  7. customdried
  8. customtriturated overnight in methylene chloride (200 ml
  9. customto remove a small amount of 5-chloroisatin byproduct)
  10. filtrationThese solids are filtered
  11. washwashed with methylene chloride
  12. customdried

Sources & evidence

ORD record
ord-345fcd9eac8441438f3d921548d50ee7
Source dataset
uspto-grants-1999_08
Patent number
US05935970

Reaction notes

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