2-Acetyl-4-aminophenol
-
2-Acetyl-4-aminophenol
structure -
-
CAS No:
50-80-6
-
Formula:
C8H9NO2
-
Chemical Name:
2-Acetyl-4-aminophenol
-
Synonyms:
Ethanone,1-(5-amino-2-hydroxyphenyl)-;Acetophenone,5′-amino-2′-hydroxy-;1-(5-Amino-2-hydroxyphenyl)ethanone;2-Acetyl-4-aminophenol;3-Acetyl-4-hydroxyaniline;5′-Amino-2′-hydroxyacetophenone;RG 14381;1-(5-Amino-2-hydroxyphenyl)ethan-1-one
-
CAS No:
2-Acetyl-4-aminophenol Use and Manufacturing
5-Acetamido-2-hydroxyacetophenone was hydrolyzed in 2N hydrochloric solution by refluxing for 6 hours, yielding 94percent of 5-amino-2-hydroxyacetophenone.5. p-Anisidine is acylated at the amino center with acetic anhydride in di- chloromethane and the acylated product was obtained in 91 percent yield . Then, Friedel Craft's acylation was carried out to get the hydroxyacetophenone derivative with acetyl chloride in the presence of anhydrous aluminium chloride in DCM. The intermediate was isolated in 70percent yield. δ-Acetamido^-hydroxyacetophenone was hydrolyzed in 2N hydrochloric solution by refluxing for 6 h, yielding 94percent of δ-amino^-hydroxyacetophenone.A suspension of [N- (3-ACETYL-4-HYDROXY-PHENYL)-] acetamide (1.029 g, 5.3 mmol) in [15percent] HC1 (1.5 ml, 6.2 mmol, 1.2 equ) was heated to reflux for 40 minutes, then cooled and neutralised with 10percent aqueous ammonia. The precipitated solid was collected by filtration as 1- (5-amino-2-hydroxy- phenyl) -ethanone (0.677 g, 84percent) a green solid. [APOS;H] nmr (400 MHz, CDC13) 2.58 (s, 3H) 3.47 (brs, 2H) 6.83 (d, [1H, ] 8.8 Hz) 6.91 (dd, 1H, 2.8+8. 8 Hz) 7.02 (d, 1H, 2.8 Hz). 13C nmr (100 MHz, [CDC13)] 27.12 [(CH3)] 115.71 (CH) 119.40 (CH) 119.87 [(Q)] 125.737 (CH) 138.40 (Q) 156.03 (Q) 204.48 [(Q). EI+ 151.] 1 [(100percent, M+) C8HGNO2] Calc. 151.0633 Found 151.0632.5-Acetamido-2-hydroxyacetophenone was hydrolyzed in 2N hydrochloric solution by refluxing for 6 hours, yielding 94percent of 5-amino-2-hydroxyacetophenone.5. p-Anisidine is acylated at the amino center with acetic anhydride in di- chloromethane and the acylated product was obtained in 91 percent yield . Then, Friedel Craft's acylation was carried out to get the hydroxyacetophenone derivative with acetyl chloride in the presence of anhydrous aluminium chloride in DCM. The intermediate was isolated in 70percent yield. δ-Acetamido^-hydroxyacetophenone was hydrolyzed in 2N hydrochloric solution by refluxing for 6 h, yielding 94percent of δ-amino^-hydroxyacetophenone.A suspension of [N- (3-ACETYL-4-HYDROXY-PHENYL)-] acetamide (1.029 g, 5.3 mmol) in [15percent] HC1 (1.5 ml, 6.2 mmol, 1.2 equ) was heated to reflux for 40 minutes, then cooled and neutralised with 10percent aqueous ammonia. The precipitated solid was collected by filtration as 1- (5-amino-2-hydroxy- phenyl) -ethanone (0.677 g, 84percent) a green solid. [APOS;H] nmr (400 MHz, CDC13) 2.58 (s, 3H) 3.47 (brs, 2H) 6.83 (d, [1H, ] 8.8 Hz) 6.91 (dd, 1H, 2.8+8. 8 Hz) 7.02 (d, 1H, 2.8 Hz). 13C nmr (100 MHz, [CDC13)] 27.12 [(CH3)] 115.71 (CH) 119.40 (CH) 119.87 [(Q)] 125.737 (CH) 138.40 (Q) 156.03 (Q) 204.48 [(Q). EI+ 151.] 1 [(100percent, M+) C8HGNO2] Calc. 151.0633 Found 151.0632.
Computed Properties
Molecular Weight:151.16
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes