3-Methoxybenzyl chloride → 1-Butyl-5-chloro-3-hydroxy-3-(3-methoxybenzyl)indolin-2-one

HRID 1523086Notes

Reaction equation

HRID 1523086 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[C:7]([CH2:16][C:17]2[CH:22]=[C:21](OC)[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)([OH:15])[C:6]1=[O:27])[CH2:2][CH2:3][CH3:4].COC1C=C(C=CC=1)CCl>>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[C:7]([OH:15])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[C:6]1=[O:27])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 699943-Methoxybenzyl chlorideHCID 863012751-Butyl-5-chloro-3-(3,5-dimethoxybenzyl)-3-hydroxyindolin-2-one

Product 1

HCID 863011211-Butyl-5-chloro-3-hydroxy-3-(3-methoxybenzyl)indolin-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 1-butyl-5-chloro-3-(3,5-dimethoxybenzyl)-3-hydroxyindolin-2-one and 3-methoxy benzyl chloride (purchased from Fisher Scientific). 1H NMR δ 7.31 (s, 1H), 7.24 (d, 1H), 7.02 (t, 1H), 6.69 (d, 1H), 6.59 (d, 1H), 6.52 (d, 1H), 6.43 (s, 1H), 3.64 (m, 4H), 3.30 (m, 2H), 3.20 (d, 1H), 1.6 (bs, OH), 1.30 (m, 2H), 1.11 (m, 2H), 0.84 (t, 3H). Calculated mass for C20H22ClNO3, 359.13. Observed 382.2 (M+Na).

Sources & evidence

ORD record
ord-94949265617a4180aff97ebd06613314
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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