Hydrochloric Acid → 3-(4-Fluorophenyl)-5-methyl-1-nitrosoindoline

HRID 717755Notes

Reaction equation

HRID 717755 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[NH:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[N:19]([O-])=[O:20].[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[N:10]([N:19]=[O:20])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 673731403-(4-Fluorophenyl)-5-methylindoline

Product 1

HCID 866919203-(4-Fluorophenyl)-5-methyl-1-nitrosoindolineYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Fluorophenyl)-5-methylindoline (0.7 g, 0.00308 mol) was dissolved in ethanol (4.2 mL) and concentrated hydrochloric acid (4.2 mL) was added at 0° C. The reaction mixture was stirred for 5 min. at 0° C. A solution of sodium nitrite (0.425 g, 0.00616 mol) in water (4.2 mL) was added at 0° C., and the reaction mixture was stirred for 2 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure, the residue basified with 10% aq. sodium hydroxide solution and the mixture extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give desired compound as a brown colored oil (0.6 g, 76% yield).

Workup

  1. stirringthe reaction mixture was stirred for 2 h at RT
  2. customAfter completion of reaction (monitored by TLC), solvent
  3. customwas removed under reduced pressure
  4. extractionthe mixture extracted with EtOAc (3×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39c79481708641358e8ea2d561b2576d
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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