Butylamine → 2-Butylamino-4,6-difluoronitrobenzene

HRID 2236976Notes

Reaction equation

HRID 2236976 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16]>CN(C=O)C>[CH2:13]([NH:17][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 669775242-Butylamino-4,6-difluoronitrobenzeneYield 130.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2,4,6-trifluoronitrobenzene (5.31 g, 30 mmol), TEA (8.37 mL, 60 mmol) and DMF (50 mL) was added dropwise a solution of n-butylamine (2.96 mL, 30 mmol) in DMF (20 mL) at rt following General Procedure G1 to obtain crude 2-butylamino-4,6-difluoronitrobenzene (9.0 g). This product was mixed with 3-diethylaminopropanol (11.1 mL, 75 mmol) and anhydrous THF (150 mL), and then powdered KOBut (8.5 g, 75 mmol) was added following General Procedure G2 to afford crude 2-butylamino-4,6-di(3-diethylaminopropoxy)nitrobenzene (15.5 g).

Sources & evidence

ORD record
ord-e684ab62f7f14931b9e49c7537da7b4e
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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