Hydrochloric Acid → HCID 131716188, compound

HRID 2352133Notes

Reaction equation

HRID 2352133 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[C:13](=[O:21])[C:12](C(O)=O)=[N:11]2)=[CH:6][CH:5]=1.S(Cl)(Cl)=[O:28].[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32].Cl.[C:37]1([CH3:43])C=CC=CC=1>C(OCC)(=O)C.C(N(CC)CC)C.N1C=CC=CC=1>[CH2:31]([N:33]([CH2:37][CH3:43])[C:34]([CH2:35][C:12]1[C:13](=[O:21])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[N:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=2)[N:11]=1)=[O:28])[CH3:32]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 10406690HCID 10406690, compound

Product 1

HCID 131716188HCID 131716188, compoundYield 33.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-fluorocinnoline-3-carboxylic acid (368 mg), thionyl chloride (179 mg) and pyridine (50 mg) were dissolved in toluene (10 ml), and the obtained solution was heated under reflux for 2 hours. After being allowed to cool to room temperature, the resultant mixture was added dropwise to a solution which was obtained by dissolving diethylamine (146 mg) and triethylamine (152 mg) in ethyl acetate (10 ml). The obtained mixture was stirred at room temperature for 3 hours, and was allowed to stand overnight. After the reaction solution was poured into diluted hydrochloric acid (30 ml) to which ice was added, the resultant mixture was extracted two times with ethyl acetate (20 ml). The organic layer was washed with a saturated aqueous sodium bicarbonate (10 ml), a saturated saline water (10 ml), and then dried over anhydrous magnesium sulfate, and was concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane-acetone) to give 143 mg of desired N,N-diethyl-1 -(4-trifluoromethoxyphenyl)-1,4-dihydro-4-oxo-5-fluorocinnoline-3-carboxyamide (yield: 33.8%). m.p., 118.5° C.

Workup

  1. temperaturethe obtained solution was heated
  2. temperatureunder reflux for 2 hours
  3. customwas obtained
  4. waitto stand overnight
  5. additionwas added
  6. extractionthe resultant mixture was extracted two times with ethyl acetate (20 ml)
  7. washThe organic layer was washed with a saturated aqueous sodium bicarbonate (10 ml)
  8. dry with materiala saturated saline water (10 ml), and then dried over anhydrous magnesium sulfate
  9. concentrationwas concentrated
  10. customThe residue was purified by silica gel column chromatography (eluent: n-hexane-acetone)

Sources & evidence

ORD record
ord-3a592d0f2c6042d09b2a115196aa56c9
Source dataset
uspto-grants-1989_10
Patent number
US04875924

Reaction notes

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