Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate

Base Information

• Chemical Name: Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate
• CAS No.: 68066-85-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Hs Code.: 2933499090
• European Community (EC) Number: 854-455-2
• DSSTox Substance ID: DTXSID80442707
• Mol file: 68066-85-3.mol

Synonyms:Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate;68066-85-3;1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester;SCHEMBL2335872;DTXSID80442707;LHPKFPPTKHGWCC-UHFFFAOYSA-N;AKOS015910194;methyl 1,2,3,4-tetrahydrocinchoninate;FT-0645624;EN300-119357;Methyl1,2,3,4-tetrahydroquinoline-4-carboxylate;A836000;Methyl 1,2,3,4-tetrahydro-4-quinolinecarboxylate;Methyl 1,2,3,4-tetrahydroxquinoline-4-carboxylate;Z1255403943

Chemical Property of Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate

Chemical Property:

• Boiling Point: 291.909 °C at 760 mmHg
• PKA: 4.03±0.40(Predicted)
• Flash Point: 130.342 °C
• PSA: 38.33000
• Density: 1.125 g/cm³
• LogP: 1.89680
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

Methyl1,2,3,4-tetrahydroquinoline-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCNC2=CC=CC=C12

Technology Process of Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate

There total 6 articles about Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate 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: 98.0%

quinoline-4-carboxylic acid methyl ester (21233-61-4) → methyl (±)-1,2,3,4-tetrahydroquinoline-4-carboxylate (68066-85-3)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic acid; In methanol; at 20 ℃; for 1h;

Reference yield: 90.0%

2-(2-nitro-phenyl)-4-oxo-butyric acid methyl ester (340269-83-2) → methyl (±)-1,2,3,4-tetrahydroquinoline-4-carboxylate (68066-85-3)

Guidance literature:

With hydrogen; 5percent Pd/C; In methanol; at 30 ℃; for 8h; under 3040.2 Torr;

DOI:10.1021/jo001761n

Reference yield:

methyl (2-nitrophenyl)acetate (30095-98-8) → methyl (±)-1,2,3,4-tetrahydroquinoline-4-carboxylate (68066-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / K₂CO₃; 18-crown-6 / acetonitrile / Heating

2.1: O₃ / -78 °C

2.2: p-TsOH; Me₂S / methanol / 0 - 20 °C

2.3: 98 percent / aq. HClO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

3.1: 90 percent / H₂ / 5percent Pd/C / methanol / 8 h / 30 °C / 3040.2 Torr

With 18-crown-6 ether; hydrogen; potassium carbonate; ozone; 5percent Pd/C; In methanol; acetonitrile;

DOI:10.1021/jo001761n

upstream raw materials:

2-(2-nitro-phenyl)-4-oxo-butyric acid methyl ester

methyl (2-nitrophenyl)acetate

methyl (+/-)-2-(2-nitrophenyl)-4-pentenoate

quinoline-4-carboxylic acid methyl ester

Downstream raw materials:

1-[2-(2,5-dichloro-phenoxy)-5-fluoro-pyridine-3-carbonyl]-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester

Refernces

• 1、 -. "AMINOACYLINDAZOLE IMMUNOMODULATORS FOR TREATMENT OF AUTOIMMUNE DISEASES". Paragraph 401. . Retrieved 2017/12/29.