HCID 86586004, compound → HCID 12230324, compound

HRID 1242132Notes

Reaction equation

HRID 1242132 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH2:14][CH2:15][CH:16]=O)([O-])=O>[C].[Pd].C(O)C>[CH3:11][O:10][C:8]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:13][CH:12]=1)[NH:1][C:15]([CH3:16])=[CH:14]2)=[O:9]

Participants

4

Reactant 1

HCID 86586004HCID 86586004, compound

Product 1

HCID 12230324HCID 12230324, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To an ethanol (10 ml) solution of methyl 4-nitro-3-(oxopropyl)benzoate (13.0 g), added is palladium-carbon (5%, 2.6 g) in a nitrogen atmosphere. This is purged with hydrogen, and further stirred at room temperature for 3 hours and then at 60° C. for 19 hours. The solid is removed through filtration, and the filtrate is concentrated. The resulting oily product is crystallized from toluene. The crystal formed is collected and dried to obtain 5-(methoxycarbonyl)-2-methylindole (8.42 g).

Workup

  1. customThis is purged with hydrogen
  2. waitat 60° C. for 19 hours
  3. customThe solid is removed through filtration
  4. concentrationthe filtrate is concentrated
  5. customThe resulting oily product is crystallized from toluene
  6. customThe crystal formed
  7. customis collected
  8. customdried

Sources & evidence

ORD record
ord-98df6db5ee8d4bbf98fc4fb7a163c4ef
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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