Pyridine → HCID 178462542, compound

HRID 553025Notes

Reaction equation

HRID 553025 reaction equation
[Na+:1].[CH2:2]([N+:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([CH3:24])([CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])[C:5]=1/[CH:25]=[CH:26]/NC1C=CC=CC=1)[CH3:3].[I-].[C:35]([CH2:38][CH2:39][CH2:40][C:41]1([CH3:53])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N+:43]([CH2:50][CH3:51])=[C:42]1[CH3:52])([OH:37])=[O:36].N1C=CC=CC=1.CCOCC>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:1].[C:35]([CH2:38][CH2:39][CH2:40][C:41]1([CH3:53])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]([CH2:50][CH3:51])/[C:42]/1=[CH:52]/[CH:26]=[CH:25]/[C:5]1[C:6]([CH3:24])([CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:21])=[O:22])[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([S:13]([OH:16])(=[O:15])=[O:14])[CH:8]=2)[N+:4]=1[CH2:2][CH3:3])([OH:37])=[O:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 671640423-(3-Carboxypropyl)-2,3-dimethyl-1-ethyl-3h-indolium iodide saltHCID 872933231-ethyl-3-methyl-2-((E)-2-phenylamino-vinyl)-5-sulfo-3-(3-sulfo-propyl)-3H-indolium sodium salt

Product 1

HCID 178462542HCID 178462542, compound

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 2 and 387 mg (1 mmol) 3-(3-carboxypropyl) -2,3-dimethyl-1-ethyl-3H-indolium iodide 3 salt were dissolved in a mixture of 10 ml acetic acid and 10 ml acetic anhydride. Subsequently, 5 ml pyridine was added. The solution was stirred under reflux for 15 minutes. After cooling to room temperature (about 20° C. to about 22° C.), 20 ml ether was added. The precipitate that was obtained, which was a mixture of the diastereomers 4.1 and 4.2, was extracted by suction, washed with ether, and dried. The residue was purified by column chromatography: RP-18: methanol/water 1/1.

Workup

  1. temperatureunder reflux for 15 minutes
  2. additionwas added
  3. customThe precipitate that was obtained
  4. additiona mixture of the diastereomers 4.1 and 4.2
  5. extractionwas extracted by suction
  6. washwashed with ether
  7. customdried
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7195d35ad4b0453ba02100497013ffef
Source dataset
uspto-grants-2011_05
Patent number
US07951959B2

Reaction notes

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