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

HRID 53144Notes

Reaction equation

HRID 53144 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>[OH:22][CH2:21][CH2:20][CH2:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=2)[NH:15][CH:14]=1

Participants

4

Reactant 2

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

Product 1

HCID 199620365-Nitro-3-(3-hydroxypropyl)-1H-indoleYield 70%

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 mol) in 100 mL of dry THF, at 0° C. under Ar. After stirring for 20 min, the mixture was quenched by the cautious addition of 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, mp 107°-110° C.: IR (KBr) 3480, 3180, 1625 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ8.60 (d, J=2.1 Hz, 1H), 8.35 (br s, 1H), 8.11 (dd, J=9.0, 2.2 Hz, 1H), 7.38 (d, J=8.9 Hz, 1H), 7.16 (m, 1H), 3.75 (t, J=6.2 Hz, 2H), 2.91 (t, J=7.2 Hz, 2H), 2.07-1.93 (m, 2H), 1.37 (br s, 1H).

Workup

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

Sources & evidence

ORD record
ord-6eda9ede0088460c8dc5078802776461
Source dataset
uspto-grants-1997_04
Patent number
US05618816

Reaction notes

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