4'-Butyryl-3'-hydroxyacetanilide

Base Information

• Chemical Name: 4'-Butyryl-3'-hydroxyacetanilide
• CAS No.: 28583-62-2
• Molecular Formula: C12H15 N O3
• Molecular Weight: 221.256
• Hs Code.: 2924299090
• European Community (EC) Number: 249-092-6
• UNII: 4KN634AQJ7
• DSSTox Substance ID: DTXSID30182782
• Nikkaji Number: J250.741B
• Wikidata: Q27259919
• Mol file: 28583-62-2.mol

Synonyms:28583-62-2;4'-Butyryl-3'-hydroxyacetanilide;N-(4-butanoyl-3-hydroxyphenyl)acetamide;N1-(4-butyryl-3-hydroxyphenyl)acetamide;Acetamide, N-[3-hydroxy-4-(1-oxobutyl)phenyl]-;UNII-4KN634AQJ7;4KN634AQJ7;EINECS 249-092-6;N-(3-Hydroxy-4-(1-oxobutyl)phenyl)acetamide;N-[3-Hydroxy-4-(1-oxobutyl)phenyl]acetamide;Acetamide, N-(3-hydroxy-4-(1-oxobutyl)phenyl)-;n-(4-butyryl-3-hydroxyphenyl)acetamide;Maybridge3_006119;Oprea1_160912;SCHEMBL8591572;DTXSID30182782;HMS1448G03;MFCD00276573;CCG-245089;IDI1_017506;4'-ACETAMIDO-2'-HYDROXYBUTYROPHENONE;FT-0629673;ACETANILIDE, 4'-BUTYRYL-3'-HYDROXY-;2-HYDROXY-4-ACETYLAMINOPHENYL PROPYL KETONE;Q27259919

Chemical Property of 4'-Butyryl-3'-hydroxyacetanilide

Chemical Property:

• Vapor Pressure: 4.59E-08mmHg at 25°C
• Melting Point: 85 °C
• Boiling Point: 431.9°Cat760mmHg
• Flash Point: 215°C
• PSA: 66.40000
• Density: 1.192g/cm³
• LogP: 2.40640
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

98%min ^*data from raw suppliers

N1-(4-butyryl-3-hydroxyphenyl)acetamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)C1=C(C=C(C=C1)NC(=O)C)O

Technology Process of 4'-Butyryl-3'-hydroxyacetanilide

There total 3 articles about 4'-Butyryl-3'-hydroxyacetanilide 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: 75.0%

3-acetamidophenyl butyrate (215949-61-4) → N-(4-butyryl-3-hydroxyphenyl)acetamide (28583-62-2)

Guidance literature:

With aluminum (III) chloride; at 150 - 175 ℃;

DOI:10.1021/jm200718m

Reference yield:

meta-hydroxyacetanilide (621-42-1) → N-(4-butyryl-3-hydroxyphenyl)acetamide (28583-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0.5 h / 20 °C

2: aluminum (III) chloride / 150 - 175 °C

With pyridine; aluminum (III) chloride; 2: Fries rearrangement;

DOI:10.1021/jm200718m

Reference yield:

butyryl chloride (141-75-3) + m-methoxyacetanilide (588-16-9) → N-(4-butyryl-3-hydroxyphenyl)acetamide (28583-62-2)

Guidance literature:

With aluminium trichloride; 1,2-dichloro-ethane;

upstream raw materials:

3-acetamidophenyl butyrate

butyryl chloride

m-methoxyacetanilide

meta-hydroxyacetanilide

Downstream raw materials:

6-butyl-3-ethyl-2-methyl-7-(2-phenoxyethoxy)quinolin-4(1H)-one

methyl-6-butyl-4-oxo-7-(2-phenoxyethoxy)-1,4-dihydroquinoline-3-carboxylate

6-butyl-3-iodo-2-methyl-7-(2-phenoxyethoxy)quinolin-4(1H)-one

6-butyl-4-ethoxy-3-iodo-2-methyl-7-(2-phenoxyethoxy)quinoline

Refernces

• 1、 Cross, R. Matthew,Namelikonda, Niranjan K.,Mutka, Tina S.,Luong, Lisa,Kyle, Dennis E.,Manetsch, Roman. "Synthesis, antimalarial activity, and structure-activity relationship of 7-(2-Phenoxyethoxy)-4(1H)-quinolones". supporting information; experimental part. p. 8321 - 8327. Retrieved 2012/02/04.
• 2、 Mizzoni,Goble,Konopka,Gelzer,Szanto,Maplesden,Brown,Boxer,Zaunius,Ziegler,DeStevens. "Structure and anticoccidial activity among some 4-hydroxyquinolinecarboxylates.". . p. 870 - 878. Retrieved 2007/10/08.