6-Ethyl-3-(hydroxymethyl)quinolin-2-ol

Base Information

• Chemical Name: 6-Ethyl-3-(hydroxymethyl)quinolin-2-ol
• CAS No.: 485337-98-2
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.241
• DSSTox Substance ID: DTXSID601262081
• Mol file: 485337-98-2.mol

Synonyms:6-Ethyl-3-(hydroxymethyl)quinolin-2-ol;485337-98-2;Oprea1_105731;DTXSID601262081;AKOS004121759;SB71287

Chemical Property of 6-Ethyl-3-(hydroxymethyl)quinolin-2-ol

Chemical Property:

• PSA: 53.35000
• LogP: 1.99510
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

6-Ethyl-3-(hydroxymethyl)quinolin-2-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CC2=C(C=C1)NC(=O)C(=C2)CO

Technology Process of 6-Ethyl-3-(hydroxymethyl)quinolin-2-ol

There total 3 articles about 6-Ethyl-3-(hydroxymethyl)quinolin-2-ol 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: 89.0%

6-ethyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (338428-47-0) → 6-ethyl-3-(hydroxymethyl)-quinolin-2(1H)-one (485337-98-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 4h;

DOI:10.1021/acs.jmedchem.1c01527

Reference yield:

2-chloro-6-ethyl-3-formylquinoline (436088-07-2) → 6-ethyl-3-(hydroxymethyl)-quinolin-2(1H)-one (485337-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; water / 12 h / 90 °C

2: sodium tetrahydroborate / methanol / 4 h / 20 °C

With sodium tetrahydroborate; water; acetic acid; In methanol;

DOI:10.1021/acs.jmedchem.1c01527

Reference yield:

N-(4-ethylphenyl)acetamide (3663-34-1) → 6-ethyl-3-(hydroxymethyl)-quinolin-2(1H)-one (485337-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate / 16 h / 0 - 90 °C

2: acetic acid; water / 12 h / 90 °C

3: sodium tetrahydroborate / methanol / 4 h / 20 °C

With sodium tetrahydroborate; water; acetic acid; trichlorophosphate; In methanol; 1: |Vilsmeier-Haack Formylation;

DOI:10.1021/acs.jmedchem.1c01527

upstream raw materials:

2-chloro-6-ethyl-3-formylquinoline

N-(4-ethylphenyl)acetamide

6-ethyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde