| Identification | More | [Name]
4'-Methoxyacetoacetanilide | [CAS]
5437-98-9 | [Synonyms]
4'-methoxyacetoacetanilide
AAPA
ACETOACET-P-ANISIDIDE
ACETO ACET P-ANISIDINE
acetoacetyl-p-acetanisidine
AKOS B029142
N-(4-METHOXYPHENYL)-3-OXOBUTANAMIDE
N-(4-METHOXYPHENYL)-3-OXO-BUTYRAMIDE
N-ACETOACETYL-4-METHOXYANILINE
N-ACETOACETYL-P-ANISIDINE
P-ACETOACETANISIDE
P-ACETOACETANISIDIDE
4’-methoxy-acetoacetanilid
4-methoxyl-n-acetoacetanilide
Acetoacetanilide, 4'-methoxy-
alpha-APA
Butanamide, N-(4-methoxyphenyl)-3-oxo-
Butanamide, N-(4-methoxyphenyl)-oxo-
n-(4-methoxyphenyl)-3-oxo-butanamid
N-(4-Methoxyphenyl)acetoacetamide | [EINECS(EC#)]
226-615-6 | [Molecular Formula]
C11H13NO3 | [MDL Number]
MFCD00008783 | [Molecular Weight]
207.23 | [MOL File]
5437-98-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RTECS ]
AK4598010 | [TSCA ]
TSCA listed | [HS Code ]
2924297099 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO VERY SLIGHTLY YELLOW POWDER | [Uses]
N-(4-Methoxyphenyl)-3-oxobutanamide is an intermediate in the synthesis of Tafenoquine-d3 Succinate is the labelled analog of Tatenoquine (T004760), a new 8-aminoquinoline with an improved therapeutic index and safety profile as compared to primaquine (P733500).Tafenoquine has the potential to become a widely used drug in the prevention and treatment of malaria infection and could replace some currently used drugs as resistant strains of Plasmodium species increase. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 11, p. 803, 1946 DOI: 10.1021/jo01176a024 | [Synthesis]
GENERAL STEPS: In a 100 mL round-bottomed flask, ethyl acetoacetate (0.03 mol) was added to a stirring solution of p-aminoanisole (0.01 mol) dissolved in 10 mL of PEG-300. The reaction mixture was refluxed at 120 °C for 1.5-2 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and subsequently extracted with cold ether (3 x 10 mL). The organic phases were combined and purified by column chromatography (eluent: hexane solution of 10-25% ethyl acetate) to afford the target product N-(4-methoxyphenyl)-3-oxobutylamide (3a-p). The structure of the final product was confirmed by methods reported in the literature. | [References]
[1] Synthetic Communications, 2000, vol. 30, # 20, p. 3709 - 3718
[2] Heterocycles, 2008, vol. 75, # 11, p. 2681 - 2701
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 14, p. 3171 - 3177
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 13, p. 1639 - 1641
[5] Journal of Chemical Sciences, 2014, vol. 126, # 1, p. 187 - 195 |
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