Hydroquinone → HCID 19831141, compound

HRID 358990Notes

Reaction equation

HRID 358990 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-36588d9856f6498d8a339cc9b897dadc
Source dataset
uspto-grants-1991_03
Patent number
US04999362

Reaction notes

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