The Chemistry of Synthetic Dyes by K Venkataraman (Eds.)

By K Venkataraman (Eds.)

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I. NAPHTHOQUINONOID DYES AND PIGMENTS CHART 13 ÇH 2 Py(a) DMF RT DMF RT CH 2 Py(a) ( < 1%) 43 44 B. D. TIL AK Whereas (CI) does not give 2,3,5,6-diphthaloyl-l,4-dithiadiene (XCIII) on treatment with DMF, it gives the latter compound when interacted with 2,3-dichloro-l,4-naphthoquinone (I) in DMF at room temperature, albeit in low yield. 2,3-Dibenzylmercapto-l,4-naphthoquinone (XCVIII) when reacted with (I) in boiling naphthalene also yields (XCIII) in low yield. 67 These reactions give the genesis of (XCIII) in the reactions described in Chart 10.

V. Acharya, and B. Suryanarayana, J. Sei. Ind. Res. (India) 14B, 394 (1955). 35 19 I. NAPHTHOQUINONOID DYES AND PIGMENTS CHART 5 < (I) C0 2 Et CHC0 2 Et 1. Hydrolysis 2. Decarboxylation Alk. KMn0 4 Cone. HNO3 Pratt C0 2 Et Tilak COOH ^COOH COOH Cone. HNO3 Boil N ^ "Me ^NT COOH 20 B. D. TILAK CHART 6 Cl -(I) „ O (XXX) CHC02Et I COMe Pyridine CH—C0 2 Et 0 COMe (XXXVIII) C02Et COMe O (XXXVI) has been improved by the use of ethyl chloroacetate instead of ethyl acetoacetate. 37 The reaction consists in heating (I), ethyl chloroacetate, and pyridine in a solvent such as dimethylformamide or dioxane at 100-110° for 2 hours.

A. Van Allan and G. A. Reynolds, J. Org. Chem. 28, 1019 (1963). o (XCII) 37 I. NAPHTHOQUINONOID DYES AND PIGMENTS D. REACTION o r (I) WITH MERCAPTANS: 3,4-PHTHALOYL-2THIAQUINOLIZINES Compound (I) is known to react with alkylmercaptans to give 2alkylmercapto-3-chloro-l,4-naphthoquinone and with arylmercaptans to give 2,3-diarylmercapto-l,4-naphthoquinones. Interaction of (I) with sodium sulfide yields 2,3,5,6-diphthaloyl-l,4-dithiadiene (XCIII). The latter on desulfurization yields (XCIV). 5 With a view to the synthesis of l-carbethoxy-3,4-phthaloyl-2thiaquinolizine (XCV), Tilak and Venkateswaran 6 ' 6 0 reacted (I) with C5H5N HSCH 2 C0 2 Et Base 1 r> CH—C0 2 Et CH 2 —C0 2 Et S^i^C02Et 2 38 B.

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