ethyl 5-(3-methoxypropoxy)-7-nitro-1H-indole-2-carboxylate → ethyl 7-amino-5-(3-methoxypropoxy)-1H-indole-2-carboxylate

HRID 504779Notes

Reaction equation

HRID 504779 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([N+:16]([O-])=O)[CH:15]=1)[NH:12][C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10]2>[C].[Pd].O1CCCC1>[NH2:16][C:14]1[CH:15]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10]2

Participants

4

Reactant 1

HCID 57476209ethyl 5-(3-methoxypropoxy)-7-nitro-1H-indole-2-carboxylate

Product 1

HCID 57476210ethyl 7-amino-5-(3-methoxypropoxy)-1H-indole-2-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-(3-methoxypropoxy)-7-nitro-1H-indole-2-carboxylate (6.15 g), 10% palladium-carbon (50% containing water, 1.0 g) and tetrahydrofuran (150 mL) was subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure. The catalyst was filtered off, and the filtrate was concentrated. The obtained crystals were washed with diisopropyl ether to give the title compound (5.41 g, yield 97%) as yellow crystals. The crystals were recrystallized from ethyl acetate-diisopropyl ether to give pale-yellow prism crystals. melting point 139-140° C.

Workup

  1. customwas subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. washThe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-5091c914d4c044338fca74cdc43327bd
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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