1H-Indole-2-carboxylic acid, 1,3-dimethyl-5-nitro-, methyl ester → HCID 86675793, compound

HRID 239903Notes

Reaction equation

HRID 239903 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([CH3:14])=[C:3]1[C:15]([O:17][CH3:18])=[O:16]>C1COCC1.[C].[Pd]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([C:15]([O:17][CH3:18])=[O:16])=[C:4]2[CH3:14]

Participants

4

Reactant 1

HCID 109118741H-Indole-2-carboxylic acid, 1,3-dimethyl-5-nitro-, methyl ester

Product 1

HCID 86675793HCID 86675793, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1,3-dimethyl-5-nitro-1H-indole-2-carboxylate (5.27 g) in THF (105 mL) was added 10% palladium carbon (50% water wet, 2.25 g), and the mixture was stirred at room temperature for 3 days under a hydrogen atmosphere (balloon). The insoluble material was filtered off and washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=7:3-hexane:ethyl acetate=3:2 (volume ratio)] to give the title compound (4.63 g, yield 98%) as an orange solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=7:3-hexane:ethyl acetate=3:2 (volume ratio)]

Sources & evidence

ORD record
ord-b7282bdd962a418685f458da32940c70
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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