3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate

Base Information

• Chemical Name: 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate
• CAS No.: 350797-56-7
• Molecular Formula: C22H23N3O4
• Molecular Weight: 393.442
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90436975
• Nikkaji Number: J2.155.662I
• Mol file: 350797-56-7.mol

Synonyms:350797-56-7;3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate;1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile;3-[7-cyano-5-(2-nitropropyl)-2,3-dihydroindol-1-yl]propyl Benzoate;3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propylbenzoate;SCHEMBL2547252;DTXSID90436975;BCP10529;MFCD17169997;AKOS015904543;DS-3685;1-[3-(benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)- 1H-Indole-7-carbonitrile;AC-26978;CS-0154055;FT-0747204;Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate;1-(3-Benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole;3-[7-cyano-5-(2-nitropropyl)-2,3-dihydro-1H-indol-1-yl]propyl benzoate;Benzoic acid 3-[7-cyano-5-(2-nitropropyl)indoline-1-yl]propyl ester

Chemical Property of 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate

Chemical Property:

• Boiling Point: 608.6±55.0 °C(Predicted)
• PKA: 7.80±0.13(Predicted)
• PSA: 99.15000
• Density: 1.27
• LogP: 3.96378
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 393.16885622
• Heavy Atom Count: 29
• Complexity: 619

Purity/Quality:

97% ^*data from raw suppliers

3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propylBenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC2=C(C(=C1)C#N)N(CC2)CCCOC(=O)C3=CC=CC=C3)[N+](=O)[O-]
• Uses: 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl Benzoate is used in the preparation of Silodosin (S465000), an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Technology Process of 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate

There total 16 articles about 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate 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:

1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole (350797-55-6) → 1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole (350797-56-7)

Guidance literature:

1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole; With pyridine; hydroxylamine hydrochloride; In tetrahydrofuran; at 50 ℃; for 1h;

With acetic anhydride; In tetrahydrofuran; at 50 ℃; for 3.5h; Reflux;

Reference yield:

1-(3-chloropropyl)-5-(2-nitropropyl)indoline-7-carbonitrile + Potassium benzoate (582-25-2) → 1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole (350797-56-7)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 90 - 135 ℃;

Reference yield:

1-indoline (496-15-1) → 1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole (350797-56-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / N,N-dimethyl-formamide / 20 - 50 °C

1.2: 6 h / 100 °C

2.1: trichlorophosphate / 0.67 h / cooling with ice

2.2: 3 h / 20 °C

2.3: 0.5 h

3.1: ammonium acetate / 1 h / Reflux

4.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 20 °C / cooling with ice

4.2: 1 h / pH 4

5.1: trichlorophosphate / 0.83 h / cooling with ice

5.2: 2.58 h / 50 °C

6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C

6.2: 3.5 h / 50 °C / Reflux

With pyridine; sodium tetrahydroborate; ethanol; hydroxylamine hydrochloride; triethylamine; trichlorophosphate; ammonium acetate; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

1-indoline

benzoic acid

1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole

1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole

Downstream raw materials:

silodosin

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile