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Psychotropic Drug Intermediate Of 4-Hydroxyindole 2380-94-1

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Psychotropic Drug Intermediate Of 4-Hydroxyindole 2380-94-1

Name: Psychotropic Drug Intermediate Of 4-Hydroxyindole 2380-94-1
Brand: Taizhou Volsen Chemical Co., Ltd.
Rating: 4.0 (31 reviews)

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Model No. :	2380-94-1
Brand Name :	VOLSENCHEM

10yrs

Taizhou, Zhejiang, China

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Product description

4-Hydroxyindole CAS number is 2380-94-1, It is an important intermediate for the synthesis of angina pectoris drug indorolol and the psychotropic drug dimethyl-4-hydroxytryptamine. His synthesis methods are roughly as follows:
1. Using 2,6-dinitrotoluene and paraformaldehyde as starting materials, 2,6-dinitrophenylethanol was synthesized by electrochemical method. Under the condition of 5-13atm hydrogen, Raney Ni reduced 2,6- Dinitrophenylethanol was used to obtain 2,6-diaminophenylethanol, 70% phosphoric acid was added, and 4-hydroxyindole was cyclized at 220 ° C to be reduced by palladium carbon to obtain 4-hydroxyindole CAS number 2380-94-1. The disadvantage of this method is that the starting material 2,6-dinitrotoluene is a tube product, the reaction requires expensive palladium reagents, and the reaction requires high temperature and pressure. The conditions are harsh, and industrial production cannot be achieved.
2. Using 2,6-dinitrotoluene as raw material, 2,6-dinitro-trans-β-dimethylaminostyrene is obtained through SN2 reaction, and 4-nitro-1H-indole- is obtained by ring closure. 1-alcohol, then reduced to give 4-nitroindole. After formylation protects the amino group, the nitro group is reduced to amino group. The amino group undergoes a diazotization reaction under the action of sodium nitrite and hydrochloric acid, and then hydrolyzes to obtain a phenolic hydroxyl group. The formyl group was removed by hydrolysis to give 4-hydroxyindole CAS 2380-94-1. Many materials used in this method are prohibited products and difficult to purchase.
3. Using 2-amino-3-nitrophenol as the raw material, diazotizing the substitution to obtain 2-bromo-3-nitrophenol, and then acetylating to obtain 2-bromo-3-nitrophenylacetate, use Iron powder reduces the nitro group to an amino group. After the amino group is protected with Tos, it is cross-coupled with an organic tin reagent under a palladium catalyst to obtain o-vinylaniline. Hydroxyindole CAS 2380-94-1. The disadvantage of this method is that the overall yield is lower and the starting material is more expensive.

4. Using 1,5,6,7-tetrahydro-4H-indole-4-one as a raw material, a nucleophilic substitution reaction occurs under the action of a base to obtain an amino protection product, and the amino protection product reacts with a halogenating reagent to obtain α -Halo ketone, α-halo ketone) undergo elimination reaction under the action of base to obtain 4-hydroxyindole derivative, and finally 4-hydroxyindole derivative is hydrolyzed and deprotected to obtain 4-hydroxyindole CAS 2380-94-1.

After comprehensive comparison, the fourth method is more scientific and reasonable

Thera. Category:Organic compound

Cas No.: 2380-94-1

Synonym: 1H-INDOLE-4-OL;4-HYDROXY-1H-INDOLE;4-INDOLOL;4-HYDROXYINDOLE;INDOL-4-OL;4-Hydroxy Indole (4-Indolol);4-Hydroxxyindole

Molecular Formula:C8H7NO

2380-94-1