Nitronaphthoquinone → HCID 21292556, compound

HRID 1077334Notes

Reaction equation

HRID 1077334 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>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

4

Reactant 2

HCID 54551NitronaphthoquinoneHCID 123364025-Nitronaphthalene-1,4-dione2×

Product 1

HCID 21292556HCID 21292556, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

49.6 g of a crude 5-nitronaphthoquinone cake (which had a water content of 50 wt% and a dry weight of 24.8 g, and comprised of 82 wt% of 5-nitronaphthoquinone and 10 wt% of 6-nitronaphthoquinone when determined under dried condition by a gas chromatography), 12.1 g of 1,3-butadiene and 49.6 g of benzene were introduced into an autoclave, which was then hermetically sealed for reaction at 80°C for 2.5 hours. The resultant reaction solution was cooled to 25°-30°C to crystalize 5-nitrotetrahydroanthraquinone, subjected to filtration, washed with 40 g of methanol, and dried to obtain 22.4 g of 5-nitrotetrahydroanthraquinone. The yield was 87.0% of the theoretical (based on the 5-nitronaphthoquinone contained in the crude starting material).

Workup

  1. dry with materialunder dried condition by a gas chromatography), 12.1 g of 1,3-butadiene and 49.6 g of benzene
  2. additionwere introduced into an autoclave, which
  3. customwas then hermetically sealed for reaction at 80°C for 2.5 hours
  4. customThe resultant reaction solution
  5. temperaturewas cooled to 25°-30°C
  6. customto crystalize 5-nitrotetrahydroanthraquinone
  7. filtrationsubjected to filtration
  8. washwashed with 40 g of methanol
  9. customdried

Sources & evidence

ORD record
ord-1ceedc3f1366484eb62f15dd92d030f3
Source dataset
uspto-grants-1976_05
Patent number
US03959318

Reaction notes

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