Acetone → HCID 86691931, compound

HRID 717781Notes

Reaction equation

HRID 717781 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=O)[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5]2.[Cl-].[NH4+].[CH3:21][C:22]([CH3:24])=O>[Zn]>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=[C:22]([CH3:24])[CH3:21])[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 86691930HCID 86691930, compound

Product 1

HCID 86691931HCID 86691931, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
0 °C

Procedure

5-Methyl-1-nitroso-2-phenylindoline (0.8 g, 0.00336 mol) was dissolved in acetone (30 mL), and to this saturated ammonium chloride solution (4.4 mL) was added. The reaction mixture was cooled to 0° C., and zinc dust (1.31 g, 0.0201 mol) was added portionwise over 30 min. at 0° C. The reaction was stirred for 1 h at RT, and after completion of reaction (monitored by TLC), the solvent was removed under reduced pressure. Water (100 mL) was added and the mixture extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain product as a yellow colored oil (0.6 g).

Workup

  1. customafter completion of reaction (monitored by TLC)
  2. customthe solvent was removed under reduced pressure
  3. additionWater (100 mL) was added
  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-25ae4aa482b24de987835ccc950ce628
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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