Methyl 3,3-dimethoxypropionate → Methyl 5-methoxy-1H-indole-3-carboxylate

HRID 1393665Notes

Reaction equation

HRID 1393665 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[CH3:12][O:13][CH:14]([O:20]C)[CH2:15][C:16](OC)=O>C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][CH:16]=[C:15]2[C:14]([O:13][CH3:12])=[O:20]

Participants

4

Reactant 2

HCID 81924Methyl 3,3-dimethoxypropionateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 23091969Methyl 5-methoxy-1H-indole-3-carboxylateYield 110.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

4-Methoxyphenylhydrazine hydrochloride (200 mg) and methyl 3,3-dimethoxypropionate (194 mg) were added to acetic acid (8.0 ml) and stirred for 4.5 hours at 70° C. The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:5→1:3) to give methyl 5-methoxy-1H-indole-3-carboxylate (259 mg, Y.:97%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:5→1:3)

Sources & evidence

ORD record
ord-44de0d4f6e924797a3c75e8190b466d4
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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