Isatin → ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate

HRID 545743Notes

Reaction equation

N1C2C(=CC=CC=2)C(=O)C1=O.[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:23])[C:16](=[O:22])[NH:17]2.BrCCC1CC1.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:23])[C:16](=[O:22])[N:17]2[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

Reactant 4

HCID 7054Isatin

HCID 7748Ethyl bromoacetate

HCID 960474-Chloroisatin

HCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 61359307ethyl (4-chloro-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate

Procedure

Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 4-chloro-1H-indole-2,3-dione, and (2-bromoethyl)cyclopropane with ethyl bromoacetate, the title compound was obtained (95%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.48 (t, 1H), 7.08 (d, 1H), 6.67 (d, 1H), 4.47 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 268.6 (M+1).

Sources & evidence

ORD record: ord-4541492fec104e4da6220c685b4663a5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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