Diisopropylethylamine → 3-fluoro-N-(4-methoxybutyl)-2-nitroaniline

HRID 1509457Notes

Reaction equation

HRID 1509457 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10].C(N(C(C)C)CC)(C)C.Cl.[CH3:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28]>C(#N)C>[F:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 879221,3-Difluoro-2-nitrobenzeneHCID 457923494-Methoxybutan-1-amine hydrochloride

Product 1

HCID 583554133-fluoro-N-(4-methoxybutyl)-2-nitroanilineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1,3-difluoro-2-nitrobenzene (3.00 g) and diisopropylethylamine (7 μl) in acetonitrile (30 ml) was added a solution of 4-methoxybutan-1-amine hydrochloride (2.51 g) in acetonitrile (10 ml), and the mixture was stirred at room temperature for 90 hr. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (2:98-25:75) was concentrated under reduced pressure to give the object product (2.90 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washa fraction eluted with ethyl acetate-hexane (2:98-25:75)
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-d358e5da25454976bb00bd8b2f564971
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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