Dichlone → HCID 178516906, compound

HRID 328601Notes

Reaction equation

HRID 328601 reaction equation
ClC1C(=O)C2C(C(=[O:13])C=1Cl)=CC=CC=2.[N+]([O-])([O-])=O.[Na+].[N+:20]([C:23]1[C:24](=[O:34])[C:25]2[C:30]([C:31](=[O:33])[CH:32]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)([O-:22])=[O:21]>CO.O>[OH:13][C:32]1[C:31](=[O:33])[C:30]2[C:25]([C:24](=[O:34])[C:23]=1[N+:20]([O-:22])=[O:21])=[CH:26][CH:27]=[CH:28][CH:29]=2

Participants

6

Reactant 3

HCID 8342DichloneHCID 24268Sodium NitrateHCID 19016853Nitro naphthoquinone

Product 1

HCID 178516906HCID 178516906, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2,3-dichloro-1,4naphthoquinone (6,83g; 0.03 mole) in methanol (40ml) was stirred during the addition of a solution of sodium nitrate (6.9g; 0.1 mole) in water (50ml) and the mixture stirred at 80° C for 3 hrs. Solution was attained after about 1 hr and the nitro naphthoquinone began to separate after 2 hrs. After cooling in ice and the yellow crystalline solid was filtered off, taken up in water (200ml), charcoalised and precipitated the product by addition of one-third the volume of concentrated hydrochloric acid, filtered off, washed well with 5N HCl and dried in vacuo over P2O5 /NaOH to give 5.30 g (81%) of material of m.p. 162°-163° C (d) which was identical to that prepared above.

Workup

  1. waitSolution was attained after about 1 hr
  2. customto separate after 2 hrs
  3. temperatureAfter cooling in ice
  4. filtrationthe yellow crystalline solid was filtered off
  5. customprecipitated the product
  6. additionby addition of one-third the volume of concentrated hydrochloric acid
  7. filtrationfiltered off
  8. washwashed well with 5N HCl
  9. dry with materialdried in vacuo over P2O5 /NaOH

Sources & evidence

ORD record
ord-1e1fd1638f7f4255bc05ea2445c5e04d
Source dataset
uspto-grants-1977_04
Patent number
US04017639

Reaction notes

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