Benzene, 2-fluoro-4-methyl-1-nitro- → 3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester

HRID 1747307Notes

Reaction equation

HRID 1747307 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][CH:18]([NH2:22])[CH2:19][CH2:20][CH3:21])[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:23])[CH2:17][CH:18]([NH:22][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH2:19][CH2:20][CH3:21])[CH3:14]

Participants

6

Reactant 3

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 81531DiisopropylethylamineHCID 75530735Hexanoic acid, 3-amino-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 594976263-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl esterYield 73.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-Fluoro-4-nitrotoluene (1.0 g, 6.5 mmol) in DMF (5 mL) were: 3-Amino-hexanoic acid ethyl ester hydrochloride (1.3 g, 6.7 mmol) and DIPEA (2.2 mL, 12.9 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by Combiflash using hexane and ethyl acetate (10% gradient) as an eluent to afford 1.4 g of the desired product as orange oil.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by Combiflash

Sources & evidence

ORD record
ord-836a387586724ecdb604e6f9f56de0bf
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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