Cyclopentylamine → 2-chloro-3-(cyclopentylamino)naphthalene-1,4-dione

HRID 1581024Notes

Reaction equation

HRID 1581024 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[C:9](=[O:20])[C:10]2[C:15]([C:16](=[O:19])[C:17]=1Cl)=[CH:14][CH:13]=[CH:12][CH:11]=2>C(O)C>[CH:1]1([NH:6][C:17]2[C:16](=[O:19])[C:15]3[C:10]([C:9](=[O:20])[C:8]=2[Cl:7])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 8342Dichlone

Product 1

HCID 3125952-chloro-3-(cyclopentylamino)naphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

18.7 G. of cyclopentylamine in 50 ml. of absolute ethanol are added dropwise while stirring at room temperature to a suspension of 22.7 g. of 2,3-dichloro-1,4-naphthoquinone in 100 ml. of absolute ethanol. After the addition, the mixture is boiled under reflux for 1 hour. The resulting dark-red mixture is then evaporated under reduced pressure. The residue is then dissolved in 600 ml. of chloroform and shaken out successively with 200 ml. of water, three times with 100 ml. of 3-N hydrochloric acid each time and three times with 100 ml. of water each time. After drying over sodium sulfate, the chloroform solution is concentrated, treated with active carbon and evaporated. After crystallization from n-hexane, 23.9 g. of 2-cyclopentylamino-3-chloro-1,4-naphthoquinone of melting point 81°-83°C. are obtained.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux for 1 hour
  3. customThe resulting dark-red mixture is then evaporated under reduced pressure
  4. dissolutionThe residue is then dissolved in 600 ml
  5. stirringof chloroform and shaken out successively with 200 ml
  6. dry with materialAfter drying over sodium sulfate
  7. concentrationthe chloroform solution is concentrated
  8. additiontreated with active carbon
  9. customevaporated
  10. customAfter crystallization from n-hexane, 23.9 g

Sources & evidence

ORD record
ord-c38ceecd4a324391ac60cf1487662b79
Source dataset
uspto-grants-1976_01
Patent number
US03935246

Reaction notes

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