Water → 5-(3-Dimethylaminopropoxy)-4-fluoro-2-nitrophenylamine

HRID 2243377Notes

Reaction equation

[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[F:10][C:11]1[C:17](F)=[CH:16][C:14]([NH2:15])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1.O>O1CCCC1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][C:17]1[C:11]([F:10])=[CH:12][C:13]([N+:19]([O-:21])=[O:20])=[C:14]([NH2:15])[CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a 250 ml three-necked flask under an argon atmosphere, 5.3 g of 3-dimethylamino-1-propanol, in solution in 100 ml of tetrahydrofuran, are cooled to 0° C. using an ice bath and then introduce 2.3 g of sodium hydride at 50% in liquid petroleum jelly. After stirring for 1 hour at 0° C., rapidly add a solution of 3 g of 4,5-difluoro-2-nitroaniline in 100 ml of tetrahydrofuran and then heat in the region of 70° C. for 1 hour. The reaction mixture is poured into 100 ml of water and extracted with three times 100 ml of ethyl acetate. The organic phase is dried over magnesium sulphate and brought to dryness under reduced pressure. The solid obtained is washed with pentane, filtered, and dried under a hood. In this way, we obtain 3.5 g of 5-(3-dimethylaminopropoxy)-4-fluoro-2-nitrophenylamine, in the form of a yellow solid with the following characteristics:

Workup

temperatureheat in the region of 70° C. for 1 hour
extractionextracted with three times 100 ml of ethyl acetate
dry with materialThe organic phase is dried over magnesium sulphate
customThe solid obtained
washis washed with pentane
filtrationfiltered
customdried under a hood

Sources & evidence

ORD record: ord-48b7fcd060f941cfa2dc3d583dc81e9f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674795B2

Reaction notes

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