Water → 5-(5-Nitro-1H-indol-1-yl)pentanoic acid

HRID 1978922Notes

Reaction equation

HRID 1978922 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:4].[OH-].[Na+].O.CCCCCC>C(Cl)(Cl)Cl>[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 14798Sodium HydroxideHCID 21202645HCID 21202645, compound

Product 1

HCID 212026445-(5-Nitro-1H-indol-1-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To 1-(4-methoxy carbonyl butyl)5-nitroindole (0.5 g) was added molar sodium hydroxide (10 ml) and the solution stirred in an oil bath at 120° C. for 90 minutes. It was then cooled, water (10 ml) added and the solution extracted with ethyl acetate (2×15 ml). The combined organic extracts were washed with water (2×10 ml) and the combined aqueous extracts were acidified with molar HCl and extracted with ethyl acetate. (3×15 ml). The organic extracts were dried over anhydrous sodium sulphate, filtered and rotary evaporated to give a yellow gum. The gum was dissolved in hot chloroform, then hexane (2 ml) added and the solution cooled on ice when yellow crystals separated. These were filtered off and washed with chloroform:hexane (50:50) followed by hexane. The crystals were dried in vacuo (0.423 g, 1.61 mmol, 81%), MP 141-2° C. TLC on silica in toluene:methanol:acetic acid (90:16:8) gave one yellow spot and when viewed under UV. Mass spec and NMR analysis were as expected.

Workup

  1. temperatureIt was then cooled
  2. extractionthe solution extracted with ethyl acetate (2×15 ml)
  3. washThe combined organic extracts were washed with water (2×10 ml)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customrotary evaporated
  8. customto give a yellow gum
  9. temperaturethe solution cooled on ice when yellow crystals
  10. customseparated
  11. filtrationThese were filtered off
  12. washwashed with chloroform:hexane (50:50)
  13. customThe crystals were dried in vacuo (0.423 g, 1.61 mmol, 81%), MP 141-2° C
  14. customTLC on silica in toluene:methanol:acetic acid (90:16:8) gave one yellow spot and when

Sources & evidence

ORD record
ord-0946445e7f3f42bdb38b15539e1f5e20
Source dataset
uspto-grants-2001_05
Patent number
US06239159B1

Reaction notes

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