Methanol → 1-(5-Carboxypentyl)-2-(N-phenyl-2-aminovinyl)-3,3-dimethylindolium bromide

HRID 1699963

Reaction equation

HRID 1699963 reaction equation
[Br-:1].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:20])([CH3:19])[C:11]=1[CH3:21])([OH:4])=[O:3].[C:22]1([NH:28][CH:29]=NC2C=CC=CC=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO.ClCCl>C(O)(=O)C>[Br-:1].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:20])([CH3:19])[C:11]=1[CH:21]=[CH:29][NH:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 94888N,N'-DiphenylformamidineHCID 155087421-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide

Product 1

HCID 700023921-(5-Carboxypentyl)-2-(N-phenyl-2-aminovinyl)-3,3-dimethylindolium bromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(5-carboxypentyl)-2,3,3-trimethylindolium bromide (1.77 g, 5 mmol) and N,N′-diphenylformamidine (1.96 g, 10 mmol) were mixed in acetic acid (15 m); the resulting mixture was then heated at reflux. The reaction was monitored by UV/VIS spectroscopy (methanol solution, product absorbance λmax 398 nm) and TLC (silica. Methanol, 20: dichloromethane, 80; product runs as a yellow streak, Rf 0.1-0.25). After 2.5 hrs the orange-red solution was then left to cool over 16 hrs, then the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica. 5-20% methanol/dichloromethane) to give the title compound [1.3] as a yellow-orange foam after drying, 1.5 g (66%).

Workup

  1. temperaturethe resulting mixture was then heated
  2. temperatureat reflux
  3. temperatureto cool over 16 hrs
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by flash chromatography (silica. 5-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-96cbf6e7930c4379b9c167607494cd9b
Source dataset
uspto-grants-2002_02
Patent number
US06348599B1

Linked notes

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