3-Methoxyphenylhydrazine hydrochloride → Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoate

HRID 1590727Notes

Reaction equation

HRID 1590727 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10]N)[CH:7]=[CH:8][CH:9]=1.[C:12]([S:16][CH2:17][C:18](=O)[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]>C(O)(C)(C)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:7]([C:17]([S:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:18]([CH2:19][C:20]([CH3:25])([CH3:26])[C:21]([O:23][CH3:24])=[O:22])[NH:10]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate

Product 1

HCID 53636575Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4.2 g of 3-methoxyphenylhydrazine hydrochloride and 4.9 g of methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate in 100 mL of t-butanol was refluxed for 18 hours. The mixture was cooled to R.T., and evaporated to dryness. The residue was suspended in ether (150 ml) and stirred for 30 min. The salts were filtered and the filtrate evaporated to dryness to give a residue which was chromatographed on flash silica gel using as eluant ethyl acetate:toluene (1:99) to isolate the title compound as the most polar product; m.p. 133° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customevaporated to dryness
  3. filtrationThe salts were filtered
  4. customthe filtrate evaporated to dryness
  5. customto give a residue which
  6. customwas chromatographed on flash silica gel using as eluant ethyl acetate:toluene (1:99)

Sources & evidence

ORD record
ord-79ae62b7e90745d0b1e534971300c88c
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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