2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 136049191, compound

HRID 1296328Notes

Reaction equation

HRID 1296328 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[NH:14][C:13]([CH:15]=[C:16]4[N:40]=[C:19]([C:20]([C:32]5[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=5)=[C:21]5[NH:31][C:24](=[CH:25][C:26]6[CH:27]=[CH:28][C:29]=2[N:30]=6)[CH:23]=[CH:22]5)[CH:18]=[CH:17]4)=[CH:12][CH:11]=3)[CH:6]=[CH:7][CH:8]=1.[C:41]([C:43]1[C:49](=O)[C:48](Cl)=[C:47](Cl)[C:45](=O)[C:44]=1[C:53]#N)#N.[CH2:55]1[CH2:59]OC[CH2:56]1>>[CH3:39][O:38][C:34]1[CH:33]=[C:32]([C:20]2[C:21]3[NH:31][C:24]([CH:25]=[C:26]4[N:30]=[C:29]([C:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=5)=[C:10]5[NH:14][C:13](=[C:15]([CH2:56][CH2:55][CH2:59][CH2:53][CH2:44][CH2:45][CH2:47][CH2:48][CH2:49][CH2:43][CH3:41])[C:16]6[CH:17]=[CH:18][C:19]=2[N:40]=6)[CH:12]=[CH:11]5)[CH:28]=[CH:27]4)=[CH:23][CH:22]=3)[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8028TetrahydrofuranHCID 135503060HCID 135503060, compound

Product 1

HCID 136049191HCID 136049191, compound

Procedure

5,15-bis-(3-Methoxy-phenyl)-porphyrin (100 mg, 0.19 mmol) is dissolved in anhydrous THF (30 mL) at −50° C. under an argon atmosphere. The organolithium reagent described above (5 mL) is added dropwise to the mixture. After 5 min the cooling bath is removed and the mixture is warmed to room temperature. After stirring at room temperature for 15 min the reaction is quenched by slow addition of water (2 mL). After 15 min the mixture is oxidized by the addition of DDQ (4 mL, 0.4 mmol, 0.1 M in THF) and stirred for a further 15 min. The mixture is filtered through alumna (neutral, Brockman grade+) and purified by column chromatography on silica gel eluting with hexane:dichloromethane (4:1 by vol.). The first fraction is collected and crystallised from methanol:dichloromethane.

Workup

  1. additionis added dropwise to the mixture
  2. customAfter 5 min the cooling bath is removed
  3. customis quenched by slow addition of water (2 mL)
  4. stirringstirred for a further 15 min
  5. filtrationThe mixture is filtered through alumna (neutral, Brockman grade+)
  6. custompurified by column chromatography on silica gel eluting with hexane:dichloromethane (4:1 by vol.)
  7. customThe first fraction is collected
  8. customcrystallised from methanol

Sources & evidence

ORD record
ord-721cc712a8664a8293458bb990cc7818
Source dataset
uspto-grants-2007_07
Patent number
US07244841B2

Reaction notes

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