2-amino-5-chloro-3-hydroxy-3-phenylindole

Base Information

• Chemical Name: 2-amino-5-chloro-3-hydroxy-3-phenylindole
• CAS No.: 24279-55-8
• Molecular Formula: C₁₄H₁₁ClN₂O
• Molecular Weight: 258.707
• Mol file: 24279-55-8.mol

Synonyms:2-amino-5-chloro-3-hydroxy-3-phenylindole

Chemical Property of 2-amino-5-chloro-3-hydroxy-3-phenylindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-5-chloro-3-hydroxy-3-phenylindole

There total 7 articles about 2-amino-5-chloro-3-hydroxy-3-phenylindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

potassium cyanide + N-(2-benzoyl-4-chlorophenyl)formamide (10352-28-0) → 2-amino-5-chloro-3-hydroxy-3-phenylindole (24279-55-8)

Guidance literature:

N-(2-benzoyl-4-chlorophenyl)formamide; With potassium hydrogencarbonate; In methanol; water; at 90 ℃; for 0.25 - 0.333333h;

potassium cyanide; In methanol; water; at 20 ℃; for 3 - 4h;

Reference yield: 80.0%

N-allyl-5-chloro-3-hydroxy-3-phenylindol-2-amine (1243153-55-0) → 2-amino-5-chloro-3-hydroxy-3-phenylindole (24279-55-8)

Guidance literature:

With rhodium(III) chloride;

Reference yield: 60.0%

5-chloro-3-hydroxy-3-phenyl-3H-indol-2-one (24284-35-3) → 2-amino-5-chloro-3-hydroxy-3-phenylindole (24279-55-8)

Guidance literature:

With 4-methyl-morpholine; t-butyldimethylsilyl amine; tin(IV) chloride; In tetrahydrofuran; dichloromethane; at 120 ℃; for 1h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ol101566h

upstream raw materials:

5-chloro-3-hydroxy-3-phenyl-3H-indol-2-one

N-(2-benzoyl-4-chlorophenyl)formamide

phenylmagnesium bromide

5-chloro-2-aminobenzophenone

Downstream raw materials:

(S)-2-amino-5-chloro-3-hydroxy-3-phenylindole

(R)-2-amino-5-chloro-3-phenylindol-3-oI

8-Chloro-2,3,4,10-tetrahydro-10-phenylpyrimido[1,2-a]indol-10-ol

Refernces

• 1、 Urgaonkar, Sameer,Cortese, Joseph F.,Barker, Robert H.,Cromwell, Mandy,Serrano, Adelfa E.,Wirth, Dyann F.,Clardy, Jon,Mazitschek, Ralph. "A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity". supporting information; experimental part. p. 3998 - 4001. Retrieved 2010/10/21.