Water → 2-(5-nitro-1H-indol-2-yl)propan-1-ol

HRID 1908533Notes

Reaction equation

HRID 1908533 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH:19]([CH3:25])[C:20](OCC)=[O:21])=[CH:13]2)([O-:9])=[O:8].O.[OH-].[Na+]>C1COCC1>[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH:19]([CH3:25])[CH2:20][OH:21])=[CH:13]2)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59129193ethyl 2-(5-nitro-1H-indol-2-yl)propanoate

Product 1

HCID 591293922-(5-nitro-1H-indol-2-yl)propan-1-olYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of LiAlH4 (1.0 M in THF, 1.2 mL, 1.2 mmol) in THF (5.3 mL) at 0° C. was added a solution of ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.20 g, 0.76 mmol) in THF (3.66 mL) dropwise. After addition, the mixture was allowed to warm up to room temperature and was stirred at room temperature for 3 h. The mixture was cooled to 0° C. Water (2 mL) was slowly added followed by careful addition of 15% NaOH (2 mL) and water (4 mL). The mixture was stirred at room temperature for 0.5 h and was then filtered through a short plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-(5-nitro-1H-indol-2-yl)propan-1-ol (0.14 g, 81%).

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled to 0° C
  3. stirringThe mixture was stirred at room temperature for 0.5 h
  4. filtrationwas then filtered through a short plug of celite
  5. customThe organic layer was separated from the aqueous layer
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-4dcdf99be7b141d19d3bf30049531acc
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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