ChemicalBook CAS DataBase List 1H-Indole-5-carboxylicacid,6-amino-,ethylester(9CI)

1H-Indole-5-carboxylicacid,6-amino-,ethylester(9CI) synthesis

7synthesis methods

Product Name:1H-Indole-5-carboxylicacid,6-amino-,ethylester(9CI)
CAS Number:174311-74-1
Molecular formula:C11H12N2O2
Molecular Weight:204.23

Benzoic acid, 5-[(1E)-2-(dimethylamino)ethenyl]-2,4-dinitro-, ethyl ester

174311-73-0
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1H-Indole-5-carboxylicacid,6-amino-,ethylester(9CI)

174311-74-1
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Yield:174311-74-1 30%

Reaction Conditions:

with hydrogen;nickel in ethanol at 20; under 2585.81 Torr; for 2 h;

Steps:

59

A mixture of (E)-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoate (15 g, 0.050 mol) and Raney Nickel (5 g) in EtOH (500 mL) was hydrogenated at room temperature under 50 psi of hydrogen for 2 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by column on silica gel to give ethyl 6-amino-1H-indole-5-carboxylate (3.0 g, 30%). ¹H NMR (DMSO-d₆) δ 10.68 (s, 1H), 7.99 (s, 1H), 7.01-7.06 (m, 1H), 6.62 (s, 1H), 6.27-6.28 (m, 1H), 6.16 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 1.32-1.27 (t, J=7.2 Hz, 3H).

References:

US2007/244159,2007,A1 Location in patent:Page/Page column 149

Benzoic acid, 5-[2-(dimethylamino)ethenyl]-2,4-dinitro-, ethyl ester

873055-32-4
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174311-74-1
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103039-34-5
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174311-74-1
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3113-72-2
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$10.00/5g

174311-74-1
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5-Methyl-2-nitro-benzoic acid ethyl ester

54064-40-3
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174311-74-1
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References