Ethyl 5-nitro-3indolepropionate → 5-Nitro-3-(3-hydroxypropyl)-1H-indole

HRID 1463338Notes

Reaction equation

HRID 1463338 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][CH:14]=[C:13]2[CH2:19][CH2:20][C:21](OCC)=[O:22])([O-:9])=[O:8]>C1COCC1>[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][CH2:21][OH:22])([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 19962040Ethyl 5-nitro-3indolepropionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 199620365-Nitro-3-(3-hydroxypropyl)-1H-indoleYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 95% LiAlH4 (2.20 g, 0.058 mol) in 60 mL of dry THF was added a solution of ethyl 5-nitro-3-indolepropionate (7.30 g, 0.028 g mol) in 100 mL of dry THF, at 0° C. under Ar. After stirring for 20 min the mixture was quenched by cautiously adding 3 mL of H2O. The resulting suspension was stirred for 10 min and then it was filtered and the filtercake was washed with additional THF. The filtrate was evaporated and the residue was taken up in ether, dried (Na2SO4) and evaporated, and the resulting solid was triturated with hexane to give the title compound (4.30 g, 70%) as a yellow solid, m.p. 107°-110° C.

Workup

  1. customat 0° C.
  2. customwas quenched
  3. additionby cautiously adding 3 mL of H2O
  4. stirringThe resulting suspension was stirred for 10 min
  5. filtrationit was filtered
  6. washthe filtercake was washed with additional THF
  7. customThe filtrate was evaporated
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customthe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-2d9b9e7bc4f14835b3a50493cb222a76
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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