Water → HCID 57983519, compound

HRID 2078322Notes

Reaction equation

HRID 2078322 reaction equation
[OH:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:8]=2[C:9]([CH3:19])([CH3:18])[C:10](=N)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].O.[OH:21]S(O)(=O)=O>>[OH:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:8]=2[C:9]([CH3:19])([CH3:18])[C:10](=[O:21])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 136188863HCID 136188863, compound

Product 1

HCID 57983519HCID 57983519, compoundYield 24%

Conditions

Temperature
80 °C

Procedure

To a mixture of ethyl 5-hydroxy-7-imino-8,8-dimethyl-7,8-dihydroquinoline-6-carboxylate (100 mg, 384 μmol) and water (3 mL, 166525 μmol), was added H2SO4 (0.02 mL, 384 μmol). The resulting mixture was then heated to 80° C. After 30 minutes, 0.1 mL of H2SO4 was added. After 90 minutes, the reaction was cooled to room temperature and extracted with EtOAc. The organic phase was washed with water and then with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give a light-yellow solid. The aqueous layer was concentrated in vacuo to give a white solid/yellow liquid. The solid was washed with EtOH and a white solid was filtered away. The filtrate was concentrated in vacuo to give a yellow solid. The solid was washed with DCM and the supernatant was decanted off. The solid was dissolved in MeOH and concentrated in vacuo to give a light-yellow solid which was washed once more with DCM and the supernatant was decanted away. The solid was placed under high-vacuum to leave a light-yellow solid which was purified by silica flash chromatography (0-10% MeOH/DCM) to give the title compound as a white crystalline solid (24 mg, 24%). MS (m/z)=262 (M+H)+. Calculated for C14H15NO4 261.3.

Workup

  1. waitAfter 90 minutes
  2. temperaturethe reaction was cooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a light-yellow solid
  8. concentrationThe aqueous layer was concentrated in vacuo
  9. customto give a white solid/yellow liquid
  10. washThe solid was washed with EtOH
  11. filtrationa white solid was filtered away
  12. concentrationThe filtrate was concentrated in vacuo
  13. customto give a yellow solid
  14. washThe solid was washed with DCM
  15. customthe supernatant was decanted off
  16. dissolutionThe solid was dissolved in MeOH
  17. concentrationconcentrated in vacuo
  18. customto give a light-yellow solid which
  19. washwas washed once more with DCM
  20. customthe supernatant was decanted away
  21. customto leave a light-yellow solid which
  22. customwas purified by silica flash chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-5b9d9174aae3485c85baa3f23b912e25
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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