Acetonitrile → 3-(5-Carboxypentyl)-1,1,2-trimethyl-1H-benzo[E]indol-3-ium iodide

HRID 252794Notes

Reaction equation

HRID 252794 reaction equation
C[C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[C:7]([CH3:12])[C:6]=2[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH:3]=1.[I:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].[C:26](#N)C>>[I-:17].[C:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N+:9]1[C:10]2[CH:2]=[CH:3][C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[C:6]=2[C:7]([CH3:26])([CH3:12])[C:8]=1[CH3:11])([OH:25])=[O:24]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 128279486-Iodohexanoic acidHCID 67262668Trimethylbenz[e]indole

Product 1

HCID 672626493-(5-Carboxypentyl)-1,1,2-trimethyl-1H-benzo[E]indol-3-ium iodideYield 75%

Conditions

Temperature
100 °C

Procedure

To a 250 mL flask were added trimethylbenz[e]indole (5.21 g, 24.9 mmol), acetonitrile (80 mL) and 6-iodohexanoic acid (6.5 g, 26.9 mmol). The mixture was heated at reflux under argon for 1 h and then approx. 70 mL of the acetonitrile was removed by distillation. The mixture was heated at 100° C. for 20 h. The green mixture of solid and liquid was cooled to rt and the volatile components were removed in vacuo. The residue was triturated with ether (2×60 mL), ethyl acetate (2×60 mL) and with ether (2×60 mL) to give 12 as a powder (8.51 g, 75%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 1 h
  3. customapprox. 70 mL of the acetonitrile was removed by distillation
  4. additionThe green mixture of solid and liquid
  5. temperaturewas cooled to rt
  6. customthe volatile components were removed in vacuo
  7. customThe residue was triturated with ether (2×60 mL), ethyl acetate (2×60 mL) and with ether (2×60 mL)

Sources & evidence

ORD record
ord-e9ff228698814be3b861bd944ad012a9
Source dataset
uspto-grants-2011_01
Patent number
US07868157B2

Reaction notes

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