1,4-Naphthoquinone → HCID 14614968, compound

HRID 273910Notes

Reaction equation

HRID 273910 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]>C1(C)C=CC=CC=1.C1(C=CC(O)=CC=1)O>[CH2:20]([O:19][C:18]([NH:17][CH:13]1[CH:2]2[CH:3]([C:4](=[O:11])[C:5]3[C:10]([C:1]2=[O:12])=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:16][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 14614968HCID 14614968, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

3.16 g of 1,4-naphthoquinone, 4.48 g of benzyl N-butadienylcarbamate and 50 mg of hydroquinone were dissolved in 100 ml of toluene and stirred at 25° C. for 8 hours and the solution was then concentrated in vacuo. The residue was taken up in chloroform, the solution was filtered through silica gel and the filtrate was concentrated in vacuo. 7.12 g of 1-benzyloxycarbonylamino-1,4,4a,9a-tetrahydroanthraquinone (93% pure; 92% of theory) were obtained.

Workup

  1. concentrationthe solution was then concentrated in vacuo
  2. filtrationthe solution was filtered through silica gel
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-be620bcbb5b1487b9e47685ab899461e
Source dataset
uspto-grants-1995_02
Patent number
US05387704

Reaction notes

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