Hydrochloric Acid → Rivoglitazone hydrochloride

HRID 424868Notes

Reaction equation

HRID 424868 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:31]=[CH:30][C:12]([O:13][CH2:14][C:15]([N:17]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=3[N+:27]([O-])=O)[CH3:18])=O)=[CH:11][CH:10]=2)[S:3]1.CO.[ClH:34].[H][H]>[C].[Pd].CC(N(C)C)=O>[ClH:34].[CH3:26][O:25][C:23]1[CH:22]=[CH:21][C:20]2[N:27]=[C:15]([CH2:14][O:13][C:12]3[CH:30]=[CH:31][C:9]([CH2:8][CH:4]4[S:3][C:2](=[O:1])[NH:6][C:5]4=[O:7])=[CH:10][CH:11]=3)[N:17]([CH3:18])[C:19]=2[CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 116622722-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}-N-(5-methoxy-2-nitrophenyl)-N-methylacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 9889104Rivoglitazone hydrochlorideYield 48%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}-N-(5-methoxy-2-nitrophenyl)-N-methylacetamide (444.7 mg) in a mixed solvent of methanol (20 ml) and dimethylacetamide (5 ml) were added successively concentrated hydrochloric acid (0.344 ml) and a 10% wet palladium-carbon catalyst (244 mg). The atmosphere in the reaction flask was replaced with hydrogen gas (5 kg/cm2), and the resulting mixture was shaken at 50° C. for 3.5 hours. After shaking, the reaction mixture was cooled to room temperature and filtered to obtain a pale yellow filtrate. When the filtrate obtained was concentrated to about 5 g, the product crystallized out of solution. The crystals precipitated were collected by filtration and washed with methanol to afford the title compound (210 mg, yield: 48%) as a white crystalline solid.

Workup

  1. stirringAfter shaking
  2. temperaturethe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto obtain a pale yellow filtrate
  5. customWhen the filtrate obtained
  6. concentrationwas concentrated to about 5 g
  7. customthe product crystallized out of solution
  8. customThe crystals precipitated
  9. filtrationwere collected by filtration
  10. washwashed with methanol

Sources & evidence

ORD record
ord-c0ccfb79e0ac40e7bea6ca21f7ee5e6c
Source dataset
uspto-grants-2012_01
Patent number
US08106079B2

Reaction notes

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