Hydrochloric Acid → HCID 58028491, compound

HRID 2408314Notes

Reaction equation

HRID 2408314 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:50]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]=[CH:52][CH:51]=2)[C:13]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][C:19]([N:26]([C:37]5[CH:42]=[CH:41][C:40]([CH:43]6OCC[O:44]6)=[CH:39][CH:38]=5)[C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[CH:30]=[CH:29][CH:28]=5)=[CH:20][CH:21]=4)[C:16]([CH3:49])([CH3:48])[C:15]=3[CH:14]=2)=[CH:8][CH:7]=1.Cl>CC(C)=O>[CH3:48][C:16]1([CH3:49])[C:17]2[CH:18]=[C:19]([N:26]([C:37]3[CH:38]=[CH:39][C:40]([CH:43]=[O:44])=[CH:41][CH:42]=3)[C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)[CH:20]=[CH:21][C:22]=2[C:23]2[C:15]1=[CH:14][C:13]([N:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=1)[C:50]1[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]=[CH:52][CH:51]=1)=[CH:25][CH:24]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58028456HCID 58028456, compound

Product 1

HCID 58028491HCID 58028491, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a three-neck round-bottom flask, were added 2.42 g N2,N7-bis(4-(1,3-dioxolan-2-yl)phenyl)-9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-9H-fluorene-2,7-diamine and in 250 mL acetone. 20 mL 2 M hydrochloric acid solution was added slowly to the reaction mixture through an addition funnel. After TLC showed the reaction was done, the solvent was removed by evaporation. 400 mL Ethyl acetate was added, and the reaction mixture was extracted using DI water (4×200 mL). The organic layer was dried over sodium sulfate. After filtration, the solvent was removed by evaporation. The product (1.7 g) was purified by flash chromatography using hexane, and 5% and up to 15% ethyl acetate in hexane. The structure was confirmed by NMR.

Workup

  1. customthe solvent was removed by evaporation
  2. addition400 mL Ethyl acetate was added
  3. extractionthe reaction mixture was extracted
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed by evaporation
  7. customThe product (1.7 g) was purified by flash chromatography

Sources & evidence

ORD record
ord-8a4eb5cf1e1b46938338c40ee1874ca7
Source dataset
uspto-grants-2014_08
Patent number
US08815639B2

Reaction notes

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