5-Methylindoline → 5-Methyl-1-nitrosoindoline
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[N:11]([O-])=[O:12].[Na+]>Cl.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=[O:12])[CH2:6][CH2:5]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
5-Methylindoline (1.0 g, 7.5 mmol) was stirred in 3N HCl (20 mL) at 0° C. Sodium nitrite (0.621 g, 9.0 mmol) in water (2 mL) was added dropwise and the mixture was stirred at 0° C. for 5 min. followed by RT for 20 min. The reaction mixture was extracted with DCM (500 mL), and the organic layer was dried over sodium sulfate and concentrated under vacuum to obtain 1.2 g of 5-methyl-1-nitrosoindoline.
Workup
- waitfollowed by RT for 20 min
- extractionThe reaction mixture was extracted with DCM (500 mL)
- dry with materialthe organic layer was dried over sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-87962a4fe92a449ba21dd06f782d09e1
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193728B2
Reaction notes
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