Hydrochloric Acid → HCID 23086711, compound

HRID 229718Notes

Reaction equation

HRID 229718 reaction equation
[OH:1][CH:2]1[CH2:11][CH:10]([C:12]([O:14]CC)=[O:13])[CH2:9][C:8]2[N:7]=[N:6][C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:4][C:3]1=2.Cl>O1CCOCC1>[OH:1][CH:2]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]2[N:7]=[N:6][C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=3)=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23086679HCID 23086679, compound

Product 1

HCID 23086711HCID 23086711, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-hydroxy-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline-7-carboxylate (60 mg, 0.164 mmol) obtained in Example 3 was dissolved in dioxane (1 mL), followed by adding 0.1 ml of a concentrated HCl solution and stirring over night. The reaction liquid was concentrated, followed by neutralization with an aqueous solution of sodium hydrogen carbonate, making weak acid using a 1N aqueous solution of sodium hydrogen sulfate, extraction with ethyl acetate, drying with sodium sulfate anhydride, filtration, concentration of thus obtained organic layer under reduced pressure and purification of residue using silica gel column chromatography (methylene chloride/methanol=10/1) to obtain an objective compound (3 mg, 5.4%).

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. extractiona 1N aqueous solution of sodium hydrogen sulfate, extraction with ethyl acetate
  4. dry with materialdrying with sodium sulfate anhydride, filtration, concentration of thus obtained organic layer under reduced pressure and purification of residue

Sources & evidence

ORD record
ord-5caf36383a174e629e572ba09ab5645c
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

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