3-(5-Nitro-indol-1-yl)-hexanoic acid ethyl ester → 3-(5-Amino-indol-1-yl)-hexanoic acid ethyl ester

HRID 23989Notes

Reaction equation

HRID 23989 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

5

Reactant 2

HCID 674273143-(5-Nitro-indol-1-yl)-hexanoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 674273453-(5-Amino-indol-1-yl)-hexanoic acid ethyl esterYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(5-nitro-indol-1-yl)-hexanoic acid ethyl ester (1.49 g, 4.9 mmol), and 10% palladium on activated carbon (149 mg) in ethanol (15 mL) was hydrogenated in a hydrogen balloon for 2 days. The mixture was filtered through Celite, and the Celite was washed with methanol. The filtrate and washing were combined, concentrated, and flash chromatographed on silica gel, eluting with EtOAc/DCM (20, 30%) to afford the title compound (1.05 g, 78% yield) as dark brown oil. 1H NMR (CDCl3) δ 7.22 (d, 1H, J=8.7 Hz), 7.05 (d, 1H, J=3.2 Hz), 6.90 (d, 1H, J=2.3 Hz), 6.66 (dd, 1H, J=2.2, 8.7 Hz), 6.33 (d, 1H, J=3.2 Hz), 4.78-4.73 (m, 1H), 4.02-3.96 (m, 2H), 3.47 (bs, 2H), 2.87-2.74 (m, 2H), 1.94-1.87 (m, 1H), 1.84-1.77 (m, 1H), 1.27-1.09 (m, 2H), 1.08 (t, 3H, J=7.1 Hz), 0.85 (t, 3H, J=7.3 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe Celite was washed with methanol
  3. washThe filtrate and washing
  4. concentrationconcentrated
  5. customflash chromatographed on silica gel
  6. washeluting with EtOAc/DCM (20, 30%)

Sources & evidence

ORD record
ord-ca9a8eb9d14b4fccb820cea6e97fe820
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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