3-Methoxybenzyl chloride → 3-Hydroxy-3-(3-methoxybenzyl)-5-methyl-1-propylindolin-2-one

HRID 1523087Notes

Reaction equation

HRID 1523087 reaction equation
C([O:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]([CH2:20][CH2:21][CH3:22])[C:11]1=[O:23])(=O)C1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl>>[OH:9][C:10]1([CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([O:25][CH3:24])[CH:27]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]([CH2:20][CH2:21][CH3:22])[C:11]1=[O:23]

Participants

3

Reactant 2

HCID 699943-Methoxybenzyl chlorideHCID 904174755-Methyl-2-oxo-1-propylindolin-3-yl benzoate

Product 1

HCID 863009713-Hydroxy-3-(3-methoxybenzyl)-5-methyl-1-propylindolin-2-one

Procedure

This compound was made in an analogous fashion to 11-ethyl-3-hydroxy-5-methyl-3-(3,4,5-trimethoxybenzyl)indolin-2-one using 5-methyl-2-oxo-1-propylindolin-3-yl benzoate and 3-methoxy benzyl chloride (purchased from Fisher Scientific). 1H NMR δ 7.12 (s, 1H), 7.04 (m, 2H), 6.69 (d, 1H), 6.55 (t, 2H), 6.43 (s, 1H), 3.61 (m, 4H), 3.29 (m, 2H), 3.16 (d, 1H), 2.89 (bs, OH), 2.32 (s, 3H), 1.39 (m, 2H), 0.74 (t, 3H). Calculated mass for C20H23NO3, 325.17. Observed 348.1 (M+Na).

Sources & evidence

ORD record
ord-27504f9be6d74ea79c60721e5cb02cef
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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