HCID 21938309, compound → HCID 11435419, compound

HRID 1242131Notes

Reaction equation

HRID 1242131 reaction equation
O=[C:2]([CH3:17])[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[N+:14]([O-])=O>C(O)(=O)C>[CH3:11][O:10][C:8]([C:7]1[CH:6]=[C:5]2[C:4]([CH:3]=[C:2]([CH3:17])[NH:14]2)=[CH:13][CH:12]=1)=[O:9]

Participants

3

Reactant 1

HCID 21938309HCID 21938309, compound

Product 1

HCID 11435419HCID 11435419, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixed solution of methyl 4-(2-oxopropyl)-3-nitrobenzoate (3.86 g), reduced iron (9.0 g) and acetic acid (40 ml) is stirred at 90° C. for 24 hours. The solid is taken out through filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain 6-methoxycarbonyl-2-methylindole (0.890 g).

Workup

  1. filtrationThe solid is taken out through filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-f899154ec640400a9338adc06aa5dd62
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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