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ChemicalBook CAS DataBase List Indigo
482-89-3

Indigo synthesis

12synthesis methods
K. Heumann treated N-phenylglycine with alkali and obtained indoxyl (keto form), which on aerial oxidation converted to indigotin. Later, a variation of the original Heumann process was made: aniline, formaldehyde, and hydrogen cyanide react to form phenylglycinonitrile, which is hydrolyzed to phenylglycine. This is the most widely used process for manufacturing indigotin. The greatest improvement in the manufacture of indigotin came when sodamide was used with alkali in the conversion of phenylglycine to indoxyl. Although there is still demand for indigotin for dyeing blue jeans, it has lost a good part of the market to other blue dyes with better dyeing properties.
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Yield:-

Steps:

Multi-step reaction with 2 steps
1: PCl5 / benzene / 4 h / Heating
2: 70 percent / thiophenol / benzene / 4 h / Heating; further thiophenols used: 1) p-CH3C6H4SH, 2) p-ClC6H4SH, 3) m-CH3C6H4SH, 4) o-CH3C6H4SH

References:

Katritzky, Alan R.;Fan, Wei-Qiang;Koziol, Anna E.;Palenik, Gus J. [Journal of Heterocyclic Chemistry,1989,vol. 26,p. 821 - 828]

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