Hydrochloric Acid → HCID 58028470, compound

HRID 42386Notes

Reaction equation

HRID 42386 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([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][CH:40]=[C:39]([CH:43]6OCC[O:44]6)[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:9]=[CH:10][CH:11]=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]=[C:39]([CH:40]=[CH:41][CH:42]=3)[CH:43]=[O:44])[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:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O: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 58028464N2,N7-bis(3-(1,3-dioxolan-2-yl)phenyl)-9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-9H-fluorene-2,7-diamine

Product 1

HCID 58028470HCID 58028470, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a three-neck round-bottom flask, were added 8.0 g N2,N7-bis(3-(1,3-dioxolan-2-yl)phenyl)-9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-9H-fluorene-2,7-diamine and in 100 mL acetone. 41.1 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. 200 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 (6.9 g) was obtained after drying under vacuum, and was carried on to next step without further purification. The structure was confirmed by NMR.

Workup

  1. customthe solvent was removed by evaporation
  2. addition200 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

Sources & evidence

ORD record
ord-fafe8098a9f844e38edafb69aafdbaef
Source dataset
uspto-grants-2013_09
Patent number
US08535974B2

Reaction notes

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