Quinone → methyl 5-hydroxy-2-(methoxymethyl)-1-methylindole-3-carboxylate

HRID 2225883Notes

Reaction equation

HRID 2225883 reaction equation
[C:1]1(=O)[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH3:9][O:10][CH2:11][C:12]([NH:18][CH3:19])=[CH:13][C:14]([O:16][CH3:17])=[O:15]>C(O)(=O)C>[OH:7][C:4]1[CH:3]=[C:2]2[C:1](=[CH:6][CH:5]=1)[N:18]([CH3:19])[C:12]([CH2:11][O:10][CH3:9])=[C:13]2[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 85255412HCID 85255412, compound

Product 1

HCID 10198835methyl 5-hydroxy-2-(methoxymethyl)-1-methylindole-3-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.1 g of 1,4-benzoquinone (28.7 mmol) was dissolved in 50 ml of acetic acid to which was subsequently added dropwise 2.28 g (14.3 mmol) of methyl 4-methoxy-3-methylamino-2-butenoate and the mixture was stirred for 5 hours at room temperature. After the solvent was distilled off under reduced pressure, the resulting residue was dissolved in ethyl acetate, washed with water and saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off and the solvent was distilled off under reduced pressure, the residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate, 2:1) to obtain 0.78 g of the title compound with a yield of 22%.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washwashed with water and saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter anhydrous magnesium sulfate was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-3523da35b3784fbbb29d60e458d8d907
Source dataset
uspto-grants-1994_09
Patent number
US05344938

Reaction notes

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