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Isatin → 3-Hydroxy-3-phenyl-1,3-dihydroindol-2-one

HRID 16620
Notes
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Reaction equation

HRID 16620 reaction equation
C([C:5]1[CH:6]=[CH:7][C:8](O)=[C:9]([C:11]2(C3C=CC=CC=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])[CH:10]=1)(C)(C)C.C1([Mg]Br)C=CC=CC=1.N1C2C(=CC=CC=2)C(=O)C1=[O:38]>C1COCC1>[OH:38][C:11]1([C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:10]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7054IsatinHCID 104060553-(5-tert-Butyl-2-hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one2×HCID 178418255HCID 178418255, compound

Product 1

HCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As another non-limiting example, 3-(5-tert-butyl-2-hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one (compound 1181) was synthesized by adding dropwise a 1M solution of phenylmagnesiumbromide (0.33 mole) to isatin (15 g, 0.1 mole) in 60 mL THF at 0° C. The resulting mixture was allowed to warm to room temperature and let stir at room temperature for 12 hours. The reaction mixture was quenched with a saturated solution of NH4Cl (100 mL) and diluted with 100 mL of dichloromethane. The layers were separated, the organic layer was washed with water followed by brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to yield 20.1 g (90 %) of 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one. A mixture of the above solid (2.5 g, 10 mmole), p-t-Bu-phenol (1.5 g, 10 mmol), p-toluenesulfonic acid (3 g) in 40 mL dichloroethane, was heated to 95° C. for six hours. The mixture was cooled and filtered. The filtrate was concentrated in vacuo to yield 2.4 g (66%) of the desired product (compound 1181).

Workup

  1. customThe reaction mixture was quenched with a saturated solution of NH4Cl (100 mL)
  2. additiondiluted with 100 mL of dichloromethane
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e729176a080341c79ac7b95818a36bac
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737172B2

Reaction notes

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