Pyranine → HCID 86652716, compound

HRID 244291

Reaction equation

HRID 244291 reaction equation
[Na+].[OH:2][C:3]1[CH:4]=[C:5]([S:27]([O-:30])(=[O:29])=[O:28])[C:6]2[CH:7]=[CH:8][C:9]3[C:18]4[C:17]=2[C:16]=1[CH:15]=[CH:14][C:13]=4[C:12]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:11][C:10]=3[S:23]([O-:26])(=[O:25])=[O:24].[Na+].[Na+].C(N(C(C)C)CC)(C)C.Br[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]CC)=[O:49]>CO>[C:48]([CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][O:2][C:3]1[CH:4]=[C:5]([S:27]([OH:30])(=[O:29])=[O:28])[C:6]2[CH:7]=[CH:8][C:9]3[C:18]4[C:17]=2[C:16]=1[CH:15]=[CH:14][C:13]=4[C:12]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:11][C:10]=3[S:23]([OH:26])(=[O:24])=[O:25])([OH:50])=[O:49]

Participants

5

Reactant 3

HCID 61388PyranineHCID 81531DiisopropylethylamineHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 86652716HCID 86652716, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-hydroxypyrene-1,3,6-trisulfonate sodium salt (2.6 g), diisopropylethylamine (2 g) and ethyl 6-bromohexanoate (7 g) in methanol (150 mL) was refluxed for 24 hours. The solvent was removed by rotary evaporation. The product was purified by HPLC. The isolated ethyl ester was redissolved in methanol (100 mL). About 0.5 g NaOH dissolved in 25 mL water was added. The resulting solution was stirred overnight. The methanol was removed by rotary evaporation. To the remaining aqueous solution was added acid until the solution became acidic. The precipitate was collected by filtration and dried under vacuum to give 8-(5-carboxypentoxy)pyrene-1,3,6-trisulfonic acid.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe solvent was removed by rotary evaporation
  3. customThe product was purified by HPLC
  4. dissolutionThe isolated ethyl ester was redissolved in methanol (100 mL)
  5. dissolutionAbout 0.5 g NaOH dissolved in 25 mL water
  6. additionwas added
  7. customThe methanol was removed by rotary evaporation
  8. additionTo the remaining aqueous solution was added acid until the solution
  9. filtrationThe precipitate was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-c7585a0d18a949378545ac71cf854edb
Source dataset
uspto-grants-2014_02
Patent number
US08658434B2

Linked notes

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