Trichloroethylene → HCID 21292556, compound

HRID 1077335Notes

Reaction equation

HRID 1077335 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:2].[N+]([C:19]1[CH:20]=C2C(=[CH:27][CH:28]=1)C(=O)C=CC2=O)([O-])=O.C=CC=C.ClC=C(Cl)Cl>O>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[C:7]1[CH2:20][CH2:19][CH2:28][CH2:27][C:8]=1[C:9]2=[O:14])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6575TrichloroethyleneHCID 78451,3-ButadieneHCID 54551NitronaphthoquinoneHCID 123364025-Nitronaphthalene-1,4-dione2×

Product 1

HCID 21292556HCID 21292556, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41.3 g of a crude 5-nitronaphthoquinone cake (having a water content of 40 wt% and a dry weight of 24.8 g, and comprised of 75 wt% of 5-nitronaphthoquinone and 15 wt% of 6-nitronaphthoquinone when determined under dried conditions), 13.1 g of 1,3-butadiene and 124 g of trichloroethylene were introduced into an autoclave. The autoclave was hermetically sealed and the reaction was effected at 80°C for 2.5 hours. Then, Example 1 was repeated to obtain 20.7 g of 5-nitrotetrahydroanthraquinone. The yield was 88.0%. The thus obtained 5-nitrotetrahydroanthraquinone was oxidized and reduced in accordance with the standard method to obtain 1-aminoanthraquinone having a purity above 98 wt% and a 2-aminoanthraquinone content of 0.5 wt%.

Workup

  1. additionwere introduced into an autoclave
  2. customThe autoclave was hermetically sealed

Sources & evidence

ORD record
ord-27e06653c355441a8b0bc17ba7c4e4af
Source dataset
uspto-grants-1976_05
Patent number
US03959318

Reaction notes

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