3-Methoxybenzyl chloride → 5-Chloro-1-ethyl-3-(3-methoxybenzyl)-2-oxoindolin-3-yl benzoate

HRID 1523084Notes

Reaction equation

HRID 1523084 reaction equation
[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[C:28](OC)[C:27](OC)=[C:26]([O:34][CH3:35])[CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16](C)[CH:17]=2)[N:12]([CH2:20][CH3:21])[C:11]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C2C(=CC=C([Cl:54])C=2)N(CC)C1=O)(=O)C1C=CC=CC=1.COC1C=C(C=CC=1)CCl>>[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:34][CH3:35])[CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:54])[CH:17]=2)[N:12]([CH2:20][CH3:21])[C:11]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 699943-Methoxybenzyl chlorideHCID 863006811-Ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoateHCID 904161685-Chloro-1-ethyl-2-oxoindolin-3-yl benzoate

Product 1

HCID 863012745-Chloro-1-ethyl-3-(3-methoxybenzyl)-2-oxoindolin-3-yl benzoate

Procedure

This compound was made in an analogous fashion to 1-ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate using 5-chloro-1-ethyl-2-oxoindolin-3-yl benzoate and 3-methoxy benzyl chloride (purchased from Fisher Scientific). 1H NMR δ 8.06 (d, 2H), 7.61 (t, 1H), 7.46 (t, 2H), 7.25 (dd, 1H), 7.09 (t, 1H), 7.02 (d, 1H), 6.76 (dd, 1H), 6.64 (m, 2H), 6.52 (s, 1H), 3.72 (m, 4H), 3.57 (m, 2H), 3.27 (d, 1H), 1.04 (t, 3H). Calculated mass for C25H22NClO4, 435.12. Observed 458.1 (M+Na).

Sources & evidence

ORD record
ord-6130dcb7a9bf4bd88a0ef16ab5da0951
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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