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Phthalides and 1,3-indandiones. XXII. Methylation of 4-nitro-2-phenylindan-1,3-dione and 4-amino-2-phenylindan-1,3-dione

P. Hrnčiar, D. Joniak, and E. Solčániová

Komenský University, Bratislava

 

Abstract:  . Methylation of 4-nitro-2-phenylindan-1,3-dione (I) and 4-amino-2-phenylindan-1,3-dione (II) with CH2N2 and MeI was studied by ir. It was detd. that in the case of I, methylation in Et2O occurs at position 3 on the O of the OH-group of the enol form of I (O-methylation) with the formation of 4-nitro-2-phenyl-3-methoxy-2-inden-1-one (III), m. 111-12°. In the case of II, the O-methylation was carried out in position 1 on the carbonyl group of II with the formation of 4-amino-2-phenyl-1-methoxy-1-inden-3-one, m. 115-16°. Methylation of the anions of I and II with MeI in abs. MeOH resulted in different products; O-methylation of I gave small amts. (6%) of III, whereas C-methylation of II occurred with the formation of 4-amino-2-methyl-2-phenylindan-1,3-dione, light yellow crystals m. 110-12°.

Full paper in Portable Document Format: 205a345.pdf (in Slovak)

 

Chemical Papers 20 (5) 345–350 (1966)

Monday, February 06, 2023

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