Hydrochloric Acid → HCID 23086688, compound

HRID 229720Notes

Reaction equation

HRID 229720 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[CH2:17][CH:16]([C:18](OCC)=[O:19])[CH2:15][C:14]2[N:13]=[N:12][C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[CH:10][C:9]1=2.Cl>C(OCC)(=O)C>[OH:19][CH2:18][CH:16]1[CH2:15][C:14]2[N:13]=[N:12][C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)=[CH:10][C:9]=2[CH:8]([OH:7])[CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 23086658HCID 23086658, compound

Product 1

HCID 23086688HCID 23086688, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of lithium aluminum hydride (14.5 mg, 0.38 mmol) in tetrahydrofran (1 mL) was added ethyl 5-oxo-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnoline-7-carboxylate (92.8 mg, 0.25 mmol) obtained in Example 2 at −40° C., followed by stirring as it is for 1 hour and gradually elevating temperature up to room temperature. Ethyl acetate (3 mL) and a 1N HCl solution (0.5 mL) were added to quench the reaction, followed by further adding distilled water (2 mL) for extraction. An organic layer obtained by washing with a saturated saline solution was dried with sodium sulfate anhydride, followed by filtering the drying agent, concentrating the organic layer under reduced pressure and purification of thus obtained residue using silica gel column chromatography (methylene chloride/methanol=10/1) to obtain an objective compound (29.9 mg, 36.3%).

Workup

  1. customup to room temperature
  2. customto quench
  3. customthe reaction
  4. additionby further adding
  5. distillationdistilled water (2 mL)
  6. extractionfor extraction
  7. customAn organic layer obtained
  8. washby washing with a saturated saline solution
  9. dry with materialwas dried with sodium sulfate anhydride
  10. filtrationby filtering the drying agent
  11. concentrationconcentrating the organic layer
  12. customunder reduced pressure and purification of thus obtained residue

Sources & evidence

ORD record
ord-b659dcdb74974028955d917937a35f26
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

Loading…