1,4-Naphthoquinone → HCID 11024734, compound

HRID 273913Notes

Reaction equation

HRID 273913 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH:13]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][CH:15]=[CH2:16]>[Cu]Cl.N1C=CC=CC=1>[CH2:20]([O:19][C:18]([NH:17][C:13]1[C:2]2[C:1](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[C:3]=2[CH:16]=[CH:15][CH:14]=1)=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 329894HCID 329894, compound

Product 1

HCID 11024734HCID 11024734, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent

Procedure

0.79 g of 1,4-naphthoquinone, 1.07 g of benzyl N-butadienylcarbamate, 25 mg of copper(I) chloride and 25 ml of pyridine were stirred at 25° C. for 30 hours under a gentle stream of air and the solution was then concentrated in vacuo. The residue was taken up in chloroform, the solution was extracted with 2N hydrochloric acid and the organic phase was concentrated in vacuo. 1.60 g of 1-benzyloxycarbonylaminoanthraquinone (83% pure; 75% of theory) were obtained.

Workup

  1. concentrationthe solution was then concentrated in vacuo
  2. extractionthe solution was extracted with 2N hydrochloric acid
  3. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-619a42ef13084a79878c82376376f7d1
Source dataset
uspto-grants-1995_02
Patent number
US05387704

Reaction notes

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