1,3-Butadiene → HCID 178514954, compound

HRID 1638491Notes

Reaction equation

HRID 1638491 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-:3])=O.[CH2:16]=[CH:17][CH:18]=[CH2:19]>>[OH:3][NH:1][C:4]1[C:5]2[C:6](=[O:15])[C:7]3[C:8](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9](=[O:14])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 78451,3-ButadieneHCID 123364025-Nitronaphthalene-1,4-dione2×

Product 1

HCID 178514954HCID 178514954, compound

Procedure

5-Nitro-1,4-naphthoquinone, referred to hereinafter for short as 5-nitronaphthoquinone, is an important dyestuff intermediate which is reacted with butadiene by a Diels-Alder reaction to 5-nitro1, 1,4,11,12-tetrahydroanthraquinone (q.v. for example N.N. Vorozhtsov et al., Zhur. Vsesoyuz. Khim. Obshchestva in D.I. Mendeleeva 5, 474 (1960) - Chem. Abstract, Vol. 55, 1547e), which is subsequently rearranged to give 1-hydroxyaminoanthraquinone or converted direct to 1-aminoanthraquinone, the starting material for numerous disperse and vat dyes (e.g. German Offenlegungsschrift 24 50 883).

Sources & evidence

ORD record
ord-cd3fb165555c4d3bab5de047fe044031
Source dataset
uspto-grants-1989_11
Patent number
US04880571

Reaction notes

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