1-Bromooctane → 1-Octyl-1H-indole-2,5-dicarboxylic acid

HRID 1829982Notes

Reaction equation

HRID 1829982 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:18]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 43083261H-indole-2,5-dicarboxylic Acid

Product 1

HCID 220564411-Octyl-1H-indole-2,5-dicarboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% suspension, 125 mg, 5 mmol) was added to a stirred solution of 1H-indole-2,5-dicarboxylic acid (525 mg, 2 mmol) in dry DMF (10 mL) and maintained at ambient temperature for 1 hour. The reaction was cooled to 0° C. and then octyl bromide (1.5 mL, 13 mmol) was added. After 3 days the reaction was quenched by addition of 5% aqueous NH4Cl. The mixture was concentrated to dryness and then purified on a silica gel column using toluene. The product was then dissolved in 30 mL ethanol and 10 mL of 2 M NaOH was added. The solution was heated at 55° C. for 2 days. The ethanol was removed in vacuo and the resulting aqueous solution was acidified with 0.01 M HCl to pH 3. The resulting precipitate was filtered and rinsed twice with water. The isolated product was dried by evaporation from absolute ethanol (3×) to give 460 mg (73%) of 84.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customAfter 3 days the reaction was quenched by addition of 5% aqueous NH4Cl
  3. concentrationThe mixture was concentrated to dryness
  4. custompurified on a silica gel column
  5. dissolutionThe product was then dissolved in 30 mL ethanol
  6. addition10 mL of 2 M NaOH was added
  7. temperatureThe solution was heated at 55° C. for 2 days
  8. customThe ethanol was removed in vacuo
  9. filtrationThe resulting precipitate was filtered
  10. washrinsed twice with water
  11. dry with materialThe isolated product was dried by evaporation from absolute ethanol (3×)

Sources & evidence

ORD record
ord-63496cf2314c41f59fb9f1771fb9f347
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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