Phenethyl bromide → 5-chloro-1-(2-phenylethyl)-1H-indole-2,3-dione

HRID 1523016Notes

Reaction equation

HRID 1523016 reaction equation
C(N1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[C:5]1=O)CC.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26].C1C=CC(CCBr)=CC=1>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:20](=[O:25])[C:19]2=[O:26]

Participants

4

Reactant 3

HCID 7666Phenethyl bromideHCID 872035-chloro-1H-indole-2,3-dioneHCID 16450901-propyl-1H-indole-2,3-dione

Product 1

HCID 29300415-chloro-1-(2-phenylethyl)-1H-indole-2,3-dione

Procedure

Was prepared in an analogous manner to 1-propylindoline-2,3-dione using the commercially available 5-chloroisatin (purchased from Fisher Scientific) and 2-phenethyl bromide (purchased from Fisher scientific). 1H NMR δ 7.54 (s, 1H), 7.44 (d, 1H), 7.27 (m, 5H), 6.64 (d, 1H), 3.95 (t, 2H), 2.99 (t, 2H).

Sources & evidence

ORD record
ord-e8460b0e9b3640079a4ffa374b616b52
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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