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

HRID 19643Notes

Reaction equation

HRID 19643 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-73db9134923e425bb135919d4807832f
Source dataset
uspto-grants-2010_06
Patent number
US07745451B2

Reaction notes

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