2-Fluoroaniline → HCID 18929233, compound

HRID 1599845Notes

Reaction equation

HRID 1599845 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][C:11]#[N:12])=[CH:8][CH:7]=1)=[O:4].[F:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>CN(C=O)C>[F:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][C:11]#[N:12])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 18929204HCID 18929204, compound

Product 1

HCID 18929233HCID 18929233, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((bromoacetyl)amino)benzyl cyanide (8.5 g, 33.6 mmol) and 2-fluoroaniline (9.03 g, 81.3 mmol) in anhydrous DMF (60 mL) was heated to 90°-100° C. for 2 days with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then extracted with CH2Cl2 (200 mL). The separated organic layer was dried (MgSO4) and filtered, a small amount of silica gel was added to the CH2Cl2 solution, and then the mixture was concentrated. Purification by chromatography, eluting with hexane-ethyl acetate (2:1), afforded 7.0 g (73.5%) of the title compound, mp 111°-113° C.: 1H NMR (DMSO-d6) δ10.09 (s, 1H), 7.61 (d, J=8.4, 2H), 7.27 (d, J=8.8, 2H), 7.05 (ddd, J=9.6, J=8.0, J=1.6, 1H), 6.94 (t, J=7.1, 1H), 6.63-6.58 (m, 2H), 5.76 (bt, J=6.0, 1H): 3.96 (s, 2H), 3.93 (d, J=6.0, 2H); 13C NMR (DMSO-d6) δ168.92, 150.87 (d, J=236), 138.18, 136.37 (d, J=11.0), 128.47, 125.85, 124.72 (d, J=3.0), 119.61, 119.32, 116.24 (d, J=6.8), 114.37 (d, J=17), 112.13, 46.62, 21.79; MS (El, m/z) 283 (M+).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with CH2Cl2 (200 mL)
  3. dry with materialThe separated organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. additiona small amount of silica gel was added to the CH2Cl2 solution
  6. concentrationthe mixture was concentrated
  7. customPurification by chromatography
  8. washeluting with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-84973b57938a4cc3aaf0cb95de873760
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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