Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate

Base Information

• Chemical Name: Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate
• CAS No.: 1422284-64-7
• Molecular Formula: C₁₂H₈F₃NO₃
• Molecular Weight: 271.196
• DSSTox Substance ID: DTXSID70372408
• Wikidata: Q82160107
• Mol file: 1422284-64-7.mol

Synonyms:Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate;123158-31-6;1422284-64-7;methyl 4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-2-carboxylate;methyl 4-oxo-6-(trifluoromethyl)-1H-quinoline-2-carboxylate;METHYL4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-2-CARBOXYLATE;Maybridge3_006676;SCHEMBL9452207;SCHEMBL19579754;DTXSID70372408;HMS1449P10;CCG-50550;MFCD00278339;AKOS015856405;SB71977;IDI1_018063;DS-17984;FT-0715601;F30808;A890853;SR-01000639918-1;Methyl 4-hydroxy-6-(trifluoromethyl)-2-quinolinecarboxylate;methyl 6-trifluoromethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate;methyl 6-trifluromethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate;methyl4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-2-carboxylate

Chemical Property of Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 271.04562760
• Heavy Atom Count: 19
• Complexity: 430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC(=O)C2=C(N1)C=CC(=C2)C(F)(F)F

Technology Process of Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate

There total 1 articles about Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-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: 56.0%

4-trifluoromethylphenylamine (455-14-1) + dimethyl acetylenedicarboxylate (762-42-5) → 6-trifluoromethyl-quinolin-4(1H)-one-2-carboxylic acid methyl ester (123158-31-6,1422284-64-7)

Guidance literature:

In ethanol; for 1h; Reflux;

DOI:10.1002/jhet.922

Reference yield:

6-trifluoromethyl-quinolin-4(1H)-one-2-carboxylic acid methyl ester (123158-31-6,1422284-64-7) → 1,4-dihydro-4-oxo-(N′-phenylcarbamoyl)-6-trifluoromethylquinoline-2-carbohydrazide (1444310-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / 5 h / Reflux

2: N,N-dimethyl-formamide / 1 h / Reflux

With hydrazine hydrate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1002/jhet.922

Reference yield:

6-trifluoromethyl-quinolin-4(1H)-one-2-carboxylic acid methyl ester (123158-31-6,1422284-64-7) → 1,4-dihydro-N′-(3-hydroxy-2-cyclohexenylidene)-4-oxo-6-trifluoromethylquinoline-2-carbohydrazide (1444310-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / 5 h / Reflux

2: N,N-dimethyl-formamide / 1 h / Reflux

With hydrazine hydrate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1002/jhet.922

upstream raw materials:

4-trifluoromethylphenylamine

dimethyl acetylenedicarboxylate

Downstream raw materials:

1,4-dihydro-4-oxo-(N′-phenylcarbamoyl)-6-trifluoromethylquinoline-2-carbohydrazide

1,4-dihydro-N′-(3-hydroxy-2-cyclohexenylidene)-4-oxo-6-trifluoromethylquinoline-2-carbohydrazide

C₂₀H₁₆F₃NO₄

4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxamide