Pyridine → 2-((E)-3-[3-(carboxy-propyl)-1-ethyl-3-methyl-1,3-dihydro-indol-(2E)-ylidene]-propenyl)-3-methyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

HRID 553023Notes

Reaction equation

HRID 553023 reaction equation
[Na+:1].[CH3:2][C:3]1([CH2:28][CH2:29][CH2:30][S:31]([OH:34])(=[O:33])=[O:32])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]([CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])=[C:4]1/[CH:19]=[CH:20]/NC1C=CC=CC=1.[I-].[C:36]([CH2:39][CH2:40][CH2:41][C:42]1([CH3:54])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N+:44]([CH2:51][CH3:52])=[C:43]1[CH3:53])([OH:38])=[O:37].N1C=CC=CC=1>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:1].[C:36]([CH2:39][CH2:40][CH2:41][C:42]1([CH3:54])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:44]([CH2:51][CH3:52])/[C:43]/1=[CH:53]/[CH:20]=[CH:19]/[C:4]1[C:3]([CH3:2])([CH2:28][CH2:29][CH2:30][S:31]([OH:34])(=[O:32])=[O:33])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])([OH:38])=[O:37]

Participants

6

Reactant 3

HCID 1049PyridineHCID 671640423-(3-Carboxypropyl)-2,3-dimethyl-1-ethyl-3h-indolium iodide saltHCID 866399813-methyl-2-((E)-2-phenylamino-vinyl)-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Product 1

HCID 1317289412-((E)-3-[3-(carboxy-propyl)-1-ethyl-3-methyl-1,3-dihydro-indol-(2E)-ylidene]-propenyl)-3-methyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

500 mg (1 mmol) 1-ethyl-3-methyl-2-((E)-2-phenylamino-vinyl)-5-sulfo-3-(3-sulfo-propyl)-3H-indolium sodium salt 8 and 387 mg (1 mmol) 3-(3-carboxypropyl)-2,3-dimethyl-1-ethyl-3H-indolium iodide salt 3 are dissolved in a mixture of 10 ml acetic acid and 10 ml acetic anhydride. Subsequently, 5 ml of pyridine is added. The solution is stirred under reflux for 15 minutes.

Workup

  1. temperatureunder reflux for 15 minutes

Sources & evidence

ORD record
ord-13ce02a4c0624d9281257dbd3cf34795
Source dataset
uspto-grants-2011_05
Patent number
US07951959B2

Reaction notes

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