Hydroquinone → HCID 19831141, compound

HRID 1493309Notes

Reaction equation

HRID 1493309 reaction equation
C([O:3][CH:4](OCC)[CH2:5][S:6][CH2:7][C:8]1[NH:9][C:10]([CH3:32])=[C:11]([C:28]([O:30][CH3:31])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.C1(C=CC(O)=CC=1)O.C(O)(=O)C(O)=O>C1COCC1>[CH:4]([CH2:5][S:6][CH2:7][C:8]1[NH:9][C:10]([CH3:32])=[C:11]([C:28]([O:30][CH3:31])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:3]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 971Oxalic AcidHCID 19831144HCID 19831144, compound

Product 1

HCID 19831141HCID 19831141, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution (25 ml) of 2-[(2,2-diethoxyethyl)-thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (5 g), hydroquinone (0.5 g), and oxalic acid (1N water solution, 10 ml) is heated to the reflux temperature, under N2 atmosphere, for one hour, then the THF is evaporated in vacuum and the water layer is extracted with AcOEt (3×20 ml). The organic phases are washed with water (2×5 ml), a satured solution of NaHCO3 (2×5 ml) and water (3×5 ml), dried on Na2SO4 and evaporated to dryness. The residue, after purification by column chromatography (SiO2 120 g; eluent: hexane/isopropyl ether 70/30), yields 3.8 g of pure 2-[(formylmethyl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine, oil.

Workup

  1. customthe THF is evaporated in vacuum
  2. extractionthe water layer is extracted with AcOEt (3×20 ml)
  3. washThe organic phases are washed with water (2×5 ml)
  4. dry with materiala satured solution of NaHCO3 (2×5 ml) and water (3×5 ml), dried on Na2SO4
  5. customevaporated to dryness
  6. customThe residue, after purification by column chromatography (SiO2 120 g; eluent: hexane/isopropyl ether 70/30)

Sources & evidence

ORD record
ord-bdac3807029343eaba694aa38146ed74
Source dataset
uspto-grants-1991_06
Patent number
US05021436

Reaction notes

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