HCID 21938309, compound → HCID 11435419, compound

HRID 1242120Notes

Reaction equation

HRID 1242120 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 removed 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. customThe solid is removed 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-8c4bdb0a539d4de7816ae9d21994a68a
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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