3,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one → 3,3-Dimethyl-6-nitroindoline

HRID 535366Notes

Reaction equation

HRID 535366 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]1=O>C1COCC1>[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

3

Reactant 1

HCID 135892273,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 219594663,3-Dimethyl-6-nitroindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3,3-dimethyl-6-nitroindolin-2-one (0.6 g, 3 mmol) (Mertens et al., J. Med. Chem. 30:1279, 1987) in THF (40 mL) at 0° C. under N2 was added 2.0 M solution of BH3.Me2S complex in THF (10 mL, 20 mmol). The mixture was stirred at rt for 10 h, and then quenched by addition of water (10 mL) and concentrated HCl (20 mL). The mixture was further stirred at rt for 5 h, and then basified with sat. aq. Na2CO3 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give an orange syrup.

Workup

  1. customquenched by addition of water (10 mL) and concentrated HCl (20 mL)
  2. stirringThe mixture was further stirred at rt for 5 h
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give an orange syrup

Sources & evidence

ORD record
ord-b1795e17ffd9438ea535fac7fac69e3b
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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