HCID 21938309, compound → HCID 11435419, compound

HRID 2187730Notes

Reaction equation

HRID 2187730 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-edb2c785a7d54b22818a5f6eb555c3b8
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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