7-ethyl-2,3-dihydro-1H-indole-2,3-dione → 7-Phenylisatin

HRID 2375517Notes

Reaction equation

HRID 2375517 reaction equation
ClC1C=CC(CC2[C:16]([OH:17])=[C:15](C(O)=O)[C:14]3[C:9](=[C:10]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=CC=1.C(C1C=CC=C2C=1NC(=[O:40])C2=O)C.C(OCC(=O)CC1C=CC(Cl)=CC=1)(=O)C.ClC1C=CC(CC2C(O)=C(C(O)=O)C3C(=C(CC)C=CC=3)N=2)=CC=1>>[C:21]1([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[NH:8][C:16](=[O:17])[C:15]3=[O:40])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 2473657-ethyl-2,3-dihydro-1H-indole-2,3-dioneHCID 111520282-(4-chlorobenzyl)-8-ethyl-3-hydroxyquinoline-4-carboxylic AcidHCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone

Product 1

HCID 107754477-PhenylisatinYield 25%

Procedure

This compound was synthesized by the procedure described above for Compound 2, reacting 7-ethyl-1H-indole-2,3-dione (1.00 g, 5.71 mmol) with intermediate 2 (1.62 g, 7.14 mmol). The crude acid was purified as described above for Compound 3 to give product as a bright yellow powder (Compound 7, 0.488 g, 25% yield): 1H NMR (400 MHz, DMSO-D6) δ 1.21 (t, J=7.5 Hz, 3H) 3.11 (q, J=7.3 Hz, 2H) 4.32 (s, 2H) 7.34 (s, 4H) 7.40 (d, J=7.1 Hz, 1H) 7.46 (t, 1H) 8.32 (d, J=8.1 Hz, 1H); HRMS (ESI+) calcd for C19H17ClNO3 (MH+) 342.0892, found 342.0890.

Workup

  1. customThis compound was synthesized by the procedure
  2. customThe crude acid was purified

Sources & evidence

ORD record
ord-beb1f9e774724089b515918872dd7fb7
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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