HCID 14614968, compound → HCID 11024734, compound

HRID 273911Notes

Reaction equation

HRID 273911 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH:25]2[CH:16]([C:17](=[O:27])[C:18]3[C:23]([C:24]2=[O:26])=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][CH:14]=[CH:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cu]Cl.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 14614968HCID 14614968, compound

Product 1

HCID 11024734HCID 11024734, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent

Procedure

0.47 g of 1-benzyloxycarbonylamino-1,4,4a,9a-tetrahydroanthraquinone, 6 mg of copper(I) chloride and 10 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. 0.41 g of 1-benzyloxycarbonylaminoanthraquinone (86% pure; 76% of theory) was 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-d963fcfe3a7549d4b179f25a147e5fff
Source dataset
uspto-grants-1995_02
Patent number
US05387704

Reaction notes

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