HCID 19962045, compound → 4-Methyl-5-nitro-3-(3-hydroxypropyl)indole

HRID 53154Notes

Reaction equation

HRID 53154 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH2:20][CH2:21][C:22](OCC)=[O:23])=[CH:11][NH:12]2>C1COCC1>[CH3:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH2:20][CH2:21][CH2:22][OH:23])=[CH:11][NH:12]2

Participants

4

Reactant 2

HCID 19962045HCID 19962045, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 199620414-Methyl-5-nitro-3-(3-hydroxypropyl)indoleYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 95% LiAlH4 (0.378 g, 9.44 mmol) in 10 mL of dry THF was added a solution of ethyl 4-methyl-5-nitro-3-indolepropionate (0.650 g, 2.36 mmol) in 2 mL of dry THF, at 0° C. under Ar. After 5 min the cooling bath was removed and stirring was continued at room temperature for 30 min. The reaction was then quenched by the sequential addition of 0.4 mL of water, 0.4 mL of 15% aqueous NaOH and finally 1.2 mL of water. The resulting suspension was diluted with ethyl acetate and then it was filtered and the filtercake was washed with additional ethyl acetate. The filtrate was evaporated and the residue was chromatographed (SiO2 /dichloromethane-ethyl acetate, 2:1) to give the title compound (0.458 g, 83%) as a solid. An analytical sample was crystallized from ethyl acetate-hexane to give yellow-orange needles, mp 129°-130° C.: IR (KBr) 3543, 3210, 1616, 1520, 1330 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.43 (br s, 1H), 7.63 (d, J=8.9 Hz, 1H), 7.30 (d, J=8.7 Hz, 1H), 7.29 (s, 1H), 4.51 (t, J=5.2 Hz, 1H), 5.20 (dt, J=6.2, 5.4 Hz, 2H), 2.91 (t, J=7.7 Hz, 2H), 2.78 (s, 3H), 1.78 (m, 2H). Anal. Calcd for C12H14N2O3 : C, 61.52; H, 6.02; N, 11.96. Found: C, 61.23; H, 5.85; N, 11.90.

Workup

  1. customat 0° C.
  2. customAfter 5 min the cooling bath was removed
  3. customThe reaction was then quenched by the sequential addition of 0.4 mL of water, 0.4 mL of 15% aqueous NaOH and finally 1.2 mL of water
  4. additionThe resulting suspension was diluted with ethyl acetate
  5. filtrationit was filtered
  6. washthe filtercake was washed with additional ethyl acetate
  7. customThe filtrate was evaporated
  8. customthe residue was chromatographed (SiO2 /dichloromethane-ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-4b46b52108c74a4793e149c5af2481b0
Source dataset
uspto-grants-1997_04
Patent number
US05618816

Reaction notes

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