Hydrochloric Acid → HCID 54466469, compound

HRID 2379491Notes

Reaction equation

HRID 2379491 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][C:34]=1[O:35]C(=O)C)[CH:8]=[CH:9][C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])=[CH:20][C:19]([CH3:30])=[CH:18][C:17]=2[CH3:31])=[O:11])(=O)C.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1CO.O.Cl>O>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]1[C:21]2[C:16](=[C:17]([CH3:31])[CH:18]=[C:19]([CH3:30])[CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[CH:32]=[CH:33][C:34]([OH:35])=[C:5]([OH:4])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 53859504HCID 53859504, compoundHCID 69597608HCID 69597608, compound

Product 1

HCID 54466469HCID 54466469, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3,4-diacetoxycinnamoylamino)-4-(2chlorophenyl)-6,8-dimethylquinoline (4.0 g), potassium carbonate (3.13 g) and dioxane-methanol-water (2:2:1, 50 ml) was stirred at room temperature for 3 hours in a stream of argon gas, then diluted with water. After being adjusted to pH 4 by addition of 2N hydrochloric acid, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed, and the residue was crystallized from isopropyl ether to give crystals of 4-(2-chlorophenyl)-3-(3,4-dihydroxycinnamoylamino)-6,8-dimethylquinoline (2.7 g, 80.4%). The crystals were recrystallized from ethyl acetate to afford pale yellowish prisms.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed
  5. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3acf2699f5944c39859e09c7eece62b1
Source dataset
uspto-grants-1994_11
Patent number
US05362742

Reaction notes

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