5-Methylindoline → HCID 20231382, compound

HRID 717782

Reaction equation

HRID 717782 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]2

Participants

5

Reactant 2

HCID 140236795-MethylindolineHCID 23668193Sodium Nitrite

Product 1

HCID 20231382HCID 20231382, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

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

  1. waitfollowed by RT for 20 min
  2. extractionThe reaction mixture was extracted with DCM (500 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-87962a4fe92a449ba21dd06f782d09e1
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Linked notes

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