Dimethylamine → 1-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one

HRID 1523057Notes

Reaction equation

HRID 1523057 reaction equation
[CH2:1]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)(=[O:18])[CH3:17].CNC>>[CH2:1]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8]([OH:9])([CH2:17][C:16](=[O:18])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 142862-AcetylpyridineHCID 15810521-butyl-1H-indole-2,3-dione

Product 1

HCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-oneYield 80%

Procedure

To a clean dry flask equipped with a stir bar was added the N-butyl isatin (0.4 grams, 1.97 mmol, 0.3 M in Methanol). 2-acetyl pyridine (0.44 mL, 3.94 mmol, purchased from Fisher Scientific) was then added to the stirring solution followed by 49 μL of dimethyl amine (40% by weight in water, purchased from Fisher Scientific). The stirring solution was stirred overnight at room temperature. The next day the solution was heated to 60° C. for 5 minutes. The solution was then concentrated and purified on a silica gel column using hexanes/ethyl acetate (2:1) to afford 0.513 grams, 80% yield. 1H-NMR δ 8.69 (d, 1H), 8.14 (d, 1H), 7.92 (t, 1H), 7.56 (m, 1H) 7.30 (m, 2H), 7.06 (t, 1H), 6.87 (d, 2H), 3.81 (d, 1H), 3.69 (m, 2H), 3.52 (d, 1H), 1.71 (m, 2H), 1.43 (m, 2H), 0.97 (t, 3H). Calculated mass for C19H20N2O3, 324.37. Observed 325.0 (M+1), 347.2 (M+Na).

Workup

  1. customTo a clean dry flask equipped with a stir bar
  2. temperatureThe next day the solution was heated to 60° C. for 5 minutes
  3. concentrationThe solution was then concentrated
  4. custompurified on a silica gel column
  5. customto afford 0.513 grams, 80% yield

Sources & evidence

ORD record
ord-cbb6767fbbc14caaa6a78bef28c06390
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

Loading…