Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate

Base Information

• Chemical Name: Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate
• CAS No.: 150535-14-1
• Molecular Formula: C11H13NO2
• European Community (EC) Number: 822-875-5
• DSSTox Substance ID: DTXSID001284881
• Mol file: 150535-14-1.mol

Synonyms:Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate;150535-14-1;SCHEMBL8905113;DTXSID001284881;AS-77065;Methyl 2,3-dihydro-1H-indole-2-acetate;CS-0161589;Methyl2-(2,3-dihydro-1H-indol-2-yl)acetate;D95150;EN300-264190

Chemical Property of Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC1CC2=CC=CC=C2N1

Technology Process of Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate

There total 8 articles about Methyl 2-(2,3-dihydro-1H-indol-2-yl)acetate 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: 67.0%

methanol (67-56-1) + (2-nitrophenyl)acetaldehyde (1969-73-9) + dibromoacetic acid (631-64-1) → 2-<(methoxycarbonyl)methyl>indoline (150535-14-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1002/jhet.1982

Reference yield: 62.0%

2-(cyanomethyl)indoline (146139-50-6) → 2-<(methoxycarbonyl)methyl>indoline (150535-14-1)

Guidance literature:

With thionyl chloride; In hydrogenchloride; methanol;

Reference yield:

indoline-2-carboxylic acid methyl ester (59040-84-5,130791-93-4,141410-06-2) → 2-<(methoxycarbonyl)methyl>indoline (150535-14-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / Heating

2: imidazole, triphenylphosphine, iodine / toluene; acetonitrile / 0.17 h

3: 37 percent / dimethylformamide / 17 h / 80 °C

4: 1.) conc. HCl, 2.) thionyl chloride / 1.) reflux, 1 h, 2.) 50 deg C, 2.5 h

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; iodine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm00049a015

upstream raw materials:

methanol

2-(cyanomethyl)indoline

indoline-2-carboxylic acid methyl ester

2,3-Dihydro-1H-indol-2-ylmethanol