Ethanol → ethyl 7-amino-1-(methoxymethyl)-1H-indole-2-carboxylate

HRID 1960236Notes

Reaction equation

HRID 1960236 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:13]([O-])=O)[CH:6]=[C:5]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(O)C>[C].[Pd].O1CCCC1>[NH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[N:4]([CH2:3][O:2][CH3:1])[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]2

Participants

5

Reactant 2

HCID 702EthanolHCID 57475941ethyl 1-(methoxymethyl)-7-nitro-1H-indole-2-carboxylate

Product 1

HCID 57475944ethyl 7-amino-1-(methoxymethyl)-1H-indole-2-carboxylateYield 91.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1-(methoxymethyl)-7-nitro-1H-indole-2-carboxylate (2.35 g), 10% palladium-carbon (0.24 g), ethanol (4 ml) and tetrahydrofuran (10 ml) was stirred overnight at room temperature under hydrogen atmosphere. The palladium-carbon was removed by filtration, and the filtrate was concentrated. The residue was subjected to silida gel column chromatography to give the title compound (1.92 g, yield 91%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). 1H-NMR(CDCl3)δ: 1.41 (3H, t, J=7.2 Hz), 3.44 (3H, s), 4.36 (2H, q, J=7.2 Hz), 4.53 (2H, brs), 6.16 (2H, s), 6.61 (1H, dd, J=7.7, 0.9 Hz), 6.97 (1H, t, J=7.7 Hz), 7.10 (1H, dd, J=7.7, 0.9 Hz), 7.28 (1H, s).

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-40f52e4e35274dc092b570ad26aed0e3
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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