107575-60-0

Usage

Uses

Used in Agrochemical Industry:
Ethyl 6-amino-5-methoxyindole-2-carboxylate is used as a key intermediate for the synthesis of various agrochemical products. Its role in this industry is to contribute to the development of effective and environmentally friendly pesticides, herbicides, and other agricultural chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Ethyl 6-amino-5-methoxyindole-2-carboxylate serves as a crucial building block for the creation of novel drugs and therapeutic agents. Its chemical structure allows for the development of compounds with potential applications in treating various medical conditions.
Used in Dyestuff Industry:
Ethyl 6-amino-5-methoxyindole-2-carboxylate is also utilized as an intermediate in the production of dyes and pigments. Its unique properties enable the synthesis of a wide range of colorants used in various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C12H14N2O3/c1-3-17-12(15)10-4-7-5-11(16-2)8(13)6-9(7)14-10/h4-6,14H,3,13H2,1-2H3

Upstream product

• 107575-59-7 ethyl pyruvate 3-formamido-4-methoxyphenyl-hydrazone 
• 78939-34-1 N-(5-amino-2-methoxylphenyl)formamide 
• 149686-06-6 N-(2-methoxyl-5-nitrophenyl)formamide 
• 99-59-2 3-amino-4-methoxynitrobenzene 
• 119825-27-3 6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester 

Downstream Products

• 910885-13-1 9-hydroxy-5-methoxyl-6,7,8,9-tetrahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester-7,9-dimethyl ester 
• 133706-80-6 5-Methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester 
• 80721-47-7 4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester 
• 72909-34-3 pyrroloquinoline quinone 

Relevant academic research and scientific papers

Preparation of PQQ in the kg Scale

The improvement of the PQQ synthesis according to the method of Corey and Tramontano allows the preparation of the triester of this cofactor in the kg scale with an overall yield of 13percent (average 78percent per step), without a bottleneck in the sequence and with crystalline, analytically pure intermediates.The new purification of free PQQ from conc.H2SO4 is remarkable with respect to the application as well as to the stability of this natural product.

Pyrroloquinoline quinone synthetic method

The invention discloses a synthetic method of pyrroloquinoline quinone. The synthetic method comprises the following steps: carrying out alkali treatment on 2-methoxy-5-nitroaniline hydrochloride as a raw material, so as to obtain a compound 1; carrying out formylation on the compound 1 under a catalysis condition of an ionic liquid, so as to obtain a compound 2; adopting sodium borohydride to reduce the compound 2 to obtain a compound 3; carrying out diazotization on the compound 3, and then enabling action between the diazotized compound 3 and HBF4 to obtain a compound 4; enabling reaction of the compound 4 and 2-methylethyl acetoacetate to obtain a compound 5; treating the compound 5 with formic acid to obtain a compound 6; carrying out amid catalysis and exchange with the ionic liquid on the compound 6 to obtain a compound 7; enabling reaction of the compound 7 and 2-oxodimethyl glutaconate to obtain a compound 8; feeding hydrogen chloride to the compound 8 under the action of Cu(OAc)2*2H2O to obtain a compound 9; carrying out basic hydrolysis on the compound 9 to obtain a compound 10. The synthetic method disclosed by the invention is cheap and accessible in raw materials, stable, high in reaction yield, quick in reaction, and easy for product separation, and is environment-friendly as the catalyst can be recycled.

SYNTHESIS OF PYRROLOQUINOLINE QUINONE (PQQ)

The invention relates to a novel nine step process for synthesizing PQQ (methoxatin). This process is efficient and reliably provides PQQ in excellent purity and high yield.

Process for dyeing keratinous fibers with aminoindoles and oxidation dye precursors at basic Ph's and dyeing agents

The invention relates to a process for dyeing keratinous fibres, which consists in applying to these fibres a composition containing, in a suitable medium for dyeing, at least one coupler of formula: STR1 where R1 denotes hydrogen or alkyl, R2 and R3 denote hydrogen, alkyl, COOR' where R' is alkyl or hydrogen, at least one of the groups R2 and R3 denoting hydrogen, R4 denotes hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl or aminoalkyl, Z1 and Z2 denote hydrogen, alkyl, hydroxyl, halogen, alkoxy, at least one of the groups Z1 and Z2 is other than hydrogen at least one oxidation dye precursor, at least one oxidizing agent, the pH of the composition applied to the fibres being higher than 7.

Method for dyeing keratinous fibres using an aminoindole in combination with a quinone derivative

Method for dyeing keratinous fibres, characterized in that at least one composition (A) containing at least one aminoindole in a medium appropriate for dyeing is applied to these fibres, the application of the composition (A) being preceded or followed by the application of a composition (B) containing, in a medium appropriate for dyeing, at least one quinone derivative chosen from ortho- or para-benzoquinones, ortho- or para-benzoquinone monoimines or diimines, 1,2- or 1,4-naphthoquinones, ortho- or para-benzoquinone sulphonimides, α,ω-alkylene-bis-1,4-benzoquinones, or 1,2- or 1,4-naphthoquinone monoimines or diimines, the aminoindoles and the quinone derivatives being chosen such that the difference in redox potential ΔE between the redox potential Ei of the aminoindoles, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the redox potential Eq of the quinone derivative, determined at pH 7 in a phosphate medium by polarography on a mercury electrode relative to the saturated calomel electrode, in such that

SYNTHESIS OF (13)C- AND (2)H-LABELLED PQQ

The scheme developed by Corey and Tramontano for the synthesis of PQQ 7 was adopted to prepare 3-(13)C-PQQ 7a. 3-(2)H-PQQ 7b could be obtained by a modification of this procedure. 8-(2)H-PQQ 7c was prepared by a different approach, applying isatin 5 in a Pfitzinger quinoline synthesis.Merits of this approach for the synthesis of radiolabelled PQQ are discussed.