Benzoyl chloride, 3,4-dichloro- → HCID 71060841, compound

HRID 528839Notes

Reaction equation

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

Participants

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-

HCID 2794655Methyl indoline-2-carboxylate

Product 1

HCID 71060841HCID 71060841, compoundYield 83%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 72A, methyl indoline-2-carboxylate (Lee, S. et al., Eur. J. Org. Chem., 38:459-471 (2003)) (3.23 g, 18.3 mmol) and 3,4-dichlorobenzoyl chloride (4.21 g, 20.1 mmol) were converted to the title compound (5.30 g, 83%) after purification using flash column chromatography (gradient from 0% to 5% EtOAc/CH2Cl2). 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 7.67 (s, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.41-7.37 (m, 1.5H), 7.23-7.20 (m, 1.5H), 7.04-7.01 (m, 2H), 5.31-5.08 (m, 1H), 3.77-3.75 (m, 3H), 3.62-3.55 (m, 1H), 3.24-3.19 (m, 1H); MS(ESI+) m/z 350.1 (M+H)+.

Sources & evidence

ORD record: ord-12c558ef3d724ab8bfb1b2e595202788
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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