| Identification | Back Directory | [Name]
Ethanone,1-(2-amino-3-methoxyphenyl)- | [CAS]
42465-54-3 | [Synonyms]
1-(2-Amino-3-methoxyphenyl)
Ethanone,1-(2-amino-3-methoxyphenyl)-
1-(2-Amino-3-methoxy-phenyl)-ethanone | [Molecular Formula]
C9H11NO2 | [MDL Number]
MFCD11113373 | [MOL File]
42465-54-3.mol | [Molecular Weight]
165.19 |
| Chemical Properties | Back Directory | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [Appearance]
White to light yellow Solid | [InChI]
InChI=1S/C9H11NO2/c1-6(11)7-4-3-5-8(12-2)9(7)10/h3-5H,10H2,1-2H3 | [InChIKey]
RHVYWYRETWKHDC-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CC=CC(OC)=C1N)C |
| Hazard Information | Back Directory | [Uses]
1-(2-Amino-3-methoxyphenyl)ethan-1-one is a versatile compound that can be used as a raw material for organic synthesis or as a component in pharmaceutical intermediates. | [General Description]
1-(2-Amino-3-methoxyphenyl)ethan-1-one can be used in the preparation of cinnoline and quinoline 4-amine derivatives. | [Synthesis]
The general steps for the synthesis of 1-(2-amino-3-methoxy-phenyl)-acetophenone from 3'-methoxy-2'-nitroacetophenone are as follows:
Step 1. Preparation of 3-methoxy-2-amino benzaldehyde
A 1:1 mixture of ethanol and acetic acid was used as reaction solvent and 3-methoxy-2-nitrobenzaldehyde (1 eq.) and iron powder (3 eq.) were added in batches. The reaction was completed within 3 hours. Upon completion of the reaction, the reaction mixture was filtered and subsequently concentrated. The concentrate was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate solution, dried and concentrated to give 2-amino-3-methoxybenzaldehyde in 85% yield.ES/MS m/z 151 (MH+). | [References]
[1] Patent: WO2007/117607, 2007, A2. Location in patent: Page/Page column 348
[2] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6873 - 6877
[3] Patent: US4620000, 1986, A
[4] Patent: US4666499, 1987, A
[5] Patent: US2011/144115, 2011, A1. Location in patent: Page/Page column 7 |
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