Trifluoroacetic acid → 7-Chloro-3-hydroxy-3-(o-tolyl)indolin-2-one

HRID 921262Notes

Reaction equation

HRID 921262 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].[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Mg]Br.O.CO.C(O)(C(F)(F)F)=O>C1COCC1>[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([OH:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:21]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 3441357-ChloroisatinHCID 22242641Methanol--water (1/1)HCID 178424303HCID 178424303, compound

Product 1

HCID 867133827-Chloro-3-hydroxy-3-(o-tolyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round-bottomed flask, a solution of 7-chloroindoline-2,3-dione (1 g, 5.51 mmol) in THF (10 mL) was cooled in an ice/water bath. A solution of o-tolylmagnesium bromide (2M, 5.51 mL, 11.01 mmol) was added, and the reaction mixture was removed from the cooling bath and warmed to room temperature. After 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give Intermediate A-20A. MS(ES): m/z=272 [M−H−]; HPLC: RT=2.478 min (H2O/MeOH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=4 min, wavelength=220 nm).

Workup

  1. customthe reaction mixture was removed from the cooling bath
  2. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give Intermediate A-20A

Sources & evidence

ORD record
ord-83e7c81fadb441b5aa3b889dc99184ba
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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