Acetone → 3-(4-fluorophenyl)-5-methyl-N-(propan-2-ylidene)indolin-1-amine

HRID 717756Notes

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)[N:10]([N:18]=O)[CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].[CH3:22][C:23]([CH3:25])=O>[Zn]>[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:18]=[C:23]([CH3:25])[CH3:22])[CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-Fluorophenyl)-5-methyl-1-nitrosoindoline (1.2 g, 0.00468 mol) was dissolved in acetone (60 mL). To this was added saturated ammonium chloride solution (6.0 mL) and the reaction mixture was cooled to 0° C. Zinc dust (1.2 g, 0.0187 mol) was added portionwise over 30 min. at 0° C. After the addition, the reaction mixture was stirred for 1 h at RT. After completion of reaction (monitored by TLC), the reaction mixture was filtered through Celite, solvent was removed under reduced pressure and the residue purified by column chromatography (8% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (0.78 g, 60% yield).

Workup

additionAfter the addition
customAfter completion of reaction (monitored by TLC)
filtrationthe reaction mixture was filtered through Celite, solvent
customwas removed under reduced pressure
customthe residue purified by column chromatography (8% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record: ord-6ce3c070926a4274ad628f7ebd192e55
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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