1-Fluoro-2-nitrobenzene → [1-(2-Nitro-phenylamino)-cyclohexyl]-acetic acid methyl ester

HRID 1747399Notes

Reaction equation

HRID 1747399 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13](=[O:22])[CH2:14][C:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:11][O:12][C:13](=[O:22])[CH2:14][C:15]1([NH:21][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 10749699Methyl 2-(1-aminocyclohexyl)acetate

Product 1

HCID 59497614[1-(2-Nitro-phenylamino)-cyclohexyl]-acetic acid methyl esterYield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-fluoro-2-nitrobenzene (450 □L, 4.3 mmol) and (1-amino-cyclohexyl)-acetic acid methyl ester (880 mg, 5.2 mmol) in DMF (5 mL) was added DIPEA (1.0 mL, 5.7 mmol). The mixture was heated at 90° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL) and washed with H2O (50 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desired [1-(2-nitro-phenylamino)-cyclohexyl]-acetic acid methyl ester (230 mg, 19%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with H2O (50 mL×3)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-28d730dab3384e5c97f84463c2c7d5e1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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