1,4-Naphthoquinone → HCID 86741863, compound

HRID 247143

Reaction equation

HRID 247143 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([C:8]([O:10][C@@H:11]2[C@H:16]([CH3:17])[O:15][C@@H:14]([CH2:18]/[CH:19]=[CH:20]/[CH:21]=[CH2:22])[CH2:13][C@@H:12]2[NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:32]1(=[O:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](=[O:42])[CH:34]=[CH:33]1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C@@H:11]2[C@H:16]([CH3:17])[O:15][C@@H:14]([CH2:18][CH:19]3[CH:33]4[CH:34]([C:35](=[O:42])[C:36]5[C:41]([C:32]4=[O:43])=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH2:22][CH:21]=[CH:20]3)[CH2:13][C@@H:12]2[NH:23][C:24](=[O:29])[C:25]([F:28])([F:26])[F:27])=[O:9])=[CH:30][CH:31]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 86741864HCID 86741864, compound

Product 1

HCID 86741863HCID 86741863, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Ninety mg (0.203 mmoles) of (E)-1-(2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-lyxo-hexopyranosyl)-2,4-pentadiene and 22.0 mg (0.140 mmoles) of 1,4 naphthoquinone were mixed in 10 ml toluene and the mixture was heated under N2 at 80°-88° C. for 4 hr. The reaction was chilled to 0° C. and filtered to give 55 mg (65%) 1,4,4a,9a-tetrahydro-1-[(2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-lyxo-hexo-pyranosyl)methyl]-anthracene-9,10-dione in impure form.

Workup

  1. temperaturethe mixture was heated under N2 at 80°-88° C. for 4 hr
  2. filtrationfiltered

Sources & evidence

ORD record
ord-98dcba6dc26745f0a09eb5fa0e55e70b
Source dataset
uspto-grants-1987_11
Patent number
US04705850

Linked notes

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