Tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Base Information

• Chemical Name: Tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate
• CAS No.: 497068-73-2
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80700591
• Wikidata: Q82632014
• Mol file: 497068-73-2.mol

Synonyms:497068-73-2;TERT-BUTYL 5-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE;tert-butyl 5-hydroxy-3,4-dihydro-2H-quinoline-1-carboxylate;tert-butyl 5-hydroxy-1,2,3,4-tetrahydroquinoline-1-carboxylate;TERT-BUTYL5-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE;SCHEMBL2885604;DTXSID80700591;IQSVBPWPSPPZPM-UHFFFAOYSA-N;AB44580;CS-0136404;FT-0708737;EN300-3204453;t-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate;Benzenepropanoic acid, .alpha.,.beta.-dibromo-4-methyl-, ethyl ester

Chemical Property of Tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Chemical Property:

• PSA: 49.77000
• LogP: 3.14490
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 249.13649347
• Heavy Atom Count: 18
• Complexity: 311

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC2=C1C=CC=C2O

Technology Process of Tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

There total 4 articles about Tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-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: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-hydroxy-1,2,3,4-tetrahydroquinoline (61468-43-7) → tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate (497068-73-2)

Guidance literature:

In 1,4-dioxane; for 24h;

Reference yield:

5-methoxyquinoline (6931-19-7) → tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate (497068-73-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / PtO₂ / methanol / 3102.89 Torr

2: BBr₃ / CH₂Cl₂ / -78 °C

3: NaOH / dioxane

With sodium hydroxide; hydrogen; boron tribromide; platinum(IV) oxide; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2006.04.004

Reference yield:

5-methoxy-1,2,3,4-tetrahydroquinoline (30389-37-8) → tert-butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate (497068-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: BBr₃ / CH₂Cl₂ / -78 °C

2: NaOH / dioxane

With sodium hydroxide; boron tribromide; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2006.04.004

upstream raw materials:

di-tert-butyl dicarbonate

5-hydroxy-1,2,3,4-tetrahydroquinoline

5-methoxy-1,2,3,4-tetrahydroquinoline

5-methoxyquinoline

Downstream raw materials:

5{3-[(chloro-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-3,4-dihydro-2H-quinoline-1-carboxylic acid ter-butyl ester

(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(1,2,3,4-tetrahydro-quinolin-5-yloxy)-propyl]-amine