Diisopropylaniline → HCID 59359518, compound

HRID 383210Notes

Reaction equation

[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[F-].[K+]>O>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 180 °C

Procedure

2,6-diisopropylaniline (25 g, 141 mmol), 2-fluoronitrobenzene (10 g, 70 mmol), and potassium fluoride (6.2 g, 106 mmol) were mixed in a one-neck flask. The mixture was heated up to 180° C. under nitrogen for 48 hours. After cooled to room temperature, water (200 mL) was added. The mixture was then extracted with dichloromethane (200 mL) for three times. The solvent was evaporated and the residue was purified by column chromatography using 20% of dichloromethane in hexanes. 10 g of desired product was obtained.

Workup

temperatureAfter cooled to room temperature
extractionThe mixture was then extracted with dichloromethane (200 mL) for three times
customThe solvent was evaporated
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-2d6bcd9c4c304632959123c0c745dea0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367223B2

Reaction notes

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