2-Acetylpyridine → 5-Chloro-3-hydroxy-1-isobutyl-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one

HRID 1523077Notes

Reaction equation

HRID 1523077 reaction equation
C(N1C2C(=CC=CC=2)C(O)([CH2:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)C1=O)CCC.[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:30](=[O:39])[C:29]2=[O:40].C(C1C=CC=CN=1)(=O)C>>[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:30](=[O:39])[C:29]2([OH:40])[CH2:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 3

HCID 142862-AcetylpyridineHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-oneHCID 47368655-Chloro-1-isobutylindoline-2,3-dione

Product 1

HCID 863005435-Chloro-3-hydroxy-1-isobutyl-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one

Procedure

This compound was made in a similar manner to 1-butyl-3-hydroxy-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one using 5-chloro-1-isobutylindoline-2,3-dione and commercially available 2-acetyl pyridine (purchased from Fisher Scientific). 1H-NMR δ 8.71 (ddd, 1H), 8.13 (dd, 1H), 7.93 (dd, 1H), 7.56 (ddd, 1H), 7.31 (d, 1H), 7.28-7.26 (m, 2H), 6.78 (d, 1H), 3.74 (dd, 1H), 3.56-3.40 (m, 3H), 2.13 (m, 1H), 0.96 (d, 6H). calculated mass for C19H19ClN2O3, 358.11, observed, 359.1 (M+1).

Sources & evidence

ORD record
ord-e177841f1b604f1f826b9ebf77c7c7c6
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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