4-Chloro-1-fluoro-2-nitrobenzene → HCID 21075428, compound

HRID 1373750Notes

Reaction equation

HRID 1373750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([NH:15][CH3:16])[CH:13]=[CH2:14]>C(#N)C>[CH2:12]([N:15]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:16])[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 69391N-Methylallylamine

Product 1

HCID 21075428HCID 21075428, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-chloro-1-fluoro-2-nitro-benzene (2.53 g, 14.41 mmol) was dissolved in anhydrous acetonitrile (80 mL). Allyl methyl amine (1.64 mL, 17.29 mmol) was added dropwise while the solution was stirred. The mixture was heated at 80° C. overnight, concentrated with silica gel powder (18 g), and purified by flash chromatography eluting with 10% ethyl acetate in hexanes (1 L) to give the title compound (3.05 g, 93%). MS (DCI) m/z 227.09 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 2.80 (s, 3 H) 3.76 (d, J=5.43 Hz, 2 H) 5.16–5.29 (m, 2 H) 5.85 (m, 1 H) 7.00 (d, J=9.16 Hz, 1 H) 7.33 (dd, J=8.99, 2.54 Hz, 1 H) 7.74 (d, J=2.71 Hz, 1 H).

Workup

  1. concentrationconcentrated with silica gel powder (18 g)
  2. custompurified by flash chromatography
  3. washeluting with 10% ethyl acetate in hexanes (1 L)

Sources & evidence

ORD record
ord-b82ecee926554664ad5e87504daea394
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

Loading…