4-Chloroisatin → 7-chloro-1-(diphenylmethyl)-1H-indole-2,3-dione

HRID 1407412Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].Cl[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=O)[C:17](=O)N2>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH:16]([C:17]1[CH:4]=[CH:3][CH:2]=[CH:10][CH:6]=1)[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:14]=1)[C:8](=[O:11])[C:7]2=[O:12]

Participants

Reactant 2

HCID 960474-Chloroisatin

HCID 3441357-Chloroisatin

Product 1

HCID 673566457-chloro-1-(diphenylmethyl)-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 4A, and making non-critical variations using 7-chloro-1H-indole-2,3-dione to replace 4-chloro-1H-indole-2,3-dione, 7-chloro-1-(diphenylmethyl)-1H-indole-2,3-dione was obtained (38%) as an orange solid: mp 172-173° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 7.71-7.60 (m, 2H), 7.36-7.27 (m, 11H), 7.22-7.17 (m, 1H).

Sources & evidence

ORD record: ord-f2481a7a4d7a403ab99317a87a4b00fe
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916580B2

Reaction notes

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