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Isatin → 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

HRID 645111
Notes
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Reaction equation

HRID 645111 reaction equation
C1(CC[N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[C:7]2=[O:16])CC1.N1C2C(=CC=CC=2)C(=O)C1=O.O1C2C=CC(O)=CC=2OC1.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1>>[Br:38][C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[C:43]([C:8]2([OH:15])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:6][C:7]2=[O:16])[CH:44]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 7054IsatinHCID 78084-BromophenolHCID 68289SesamolHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 120043333-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with isatin, 1,3-benzodioxol-5-ol with 4-bromophenol, the title compound was obtained (71%) as a yellowish solid: MS (ES+) m/z 319.4 (M+1), 321.4 (M+1).

Sources & evidence

ORD record
ord-129cd8889cad4337845e3a7f3db2bdbb
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700641B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes