Diethylene Glycol Monoethyl Ether → Carbazole-4-carboxamide

HRID 51309

Reaction equation

HRID 51309 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]([C:14]([NH2:16])=[O:15])[CH2:3][CH2:2]1.CCOCCOCCO>[Pd]>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([C:14]([NH2:16])=[O:15])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8146Diethylene Glycol Monoethyl EtherHCID 227387261,2,3,4-Tetrahydrocarbazole-4-carboxamide

Product 1

HCID 22741084Carbazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 1,2,3,4-tetrahydrocarbazole-4-carboxamide or 4-carboxhydrazide (13) is dehydrogenated by refluxing in a solvent such as carbitol in the presence of Pd/C to produce the carbazole-4-carboxamide. Alternately, treatment of (13) with DDQ in an appropriate solvent such as dioxane yields carbozole (14).

Sources & evidence

ORD record
ord-e2aea2db344f4e39a90a1ead566dea0c
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Linked notes

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