2-(Ethylamino)ethanol → 2-[{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}(ethyl)amino]ethanol

HRID 1014313Notes

Reaction equation

HRID 1014313 reaction equation
Br[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:25]([NH:27][CH2:28][CH2:29][OH:30])[CH3:26]>ClCCl>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]2[C:3](=[O:4])[CH2:2][N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][OH:30])=[CH:9][C:10]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 80722-(Ethylamino)ethanolHCID 11430Potassium CarbonateHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 594419582-[{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}(ethyl)amino]ethanolYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (4.0 g, 12.7 mmol) was dissolved in 50 mL of dicholomethane, then K2CO3 (4.4 g, 31.7 mmol) and 2-(ethylamino)ethanol (2.3 g, 25.4 mmol) in 10 mL dichloromethane were added, the reaction was stirred at RT for 3 hours. After filtration, the organic layers were washed with water (2×100 mL)and dried over Na2SO4. The solvent was removed to yield the 2-[{2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}(ethyl)amino]ethanol as a yellow solid (3.77 g, 92%).1HNMR (400 MHz, DMSO-d6) δ ppm: 0.94 (t, J=7.14 Hz,3 H), 2.45 (s, 2 H), 2.60 (m, 4 H), 3.18 (t, J=8.42 Hz, 2 H), 3.40 (t, J=6.13 Hz,2H), 3.84 (s, 3 H), 4.19 (t, J=8.51 Hz, 2 H), 7.29 (s, 1 H), 8.43 (s, 1 H).

Workup

  1. filtrationAfter filtration
  2. washthe organic layers were washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-fecab98984bb444c944e18c3d09c71f3
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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