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

HRID 1960401Notes

Reaction equation

HRID 1960401 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-00c0ba0e7bc84b21ac33aae5828b1073
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

Loading…