2-Fluoroaniline → HCID 9099167, compound

HRID 1599846Notes

Reaction equation

HRID 1599846 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[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:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 586678HCID 586678, compound

Product 1

HCID 9099167HCID 9099167, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((bromoacetyl)amino)nitrobenzene (12.0 g, 46.3 mmol) and 2-fluoroaniline (11.0 g, 102 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 organic layer was dried (MgSO4) and filtered, a small amount of silica gel was added to the CH2 Cl2 solution, and then the mixture was concentrated. Purification by chromatography, eluting with hexane-ethyl acetate (3:1), afforded 8.54 g (63.7%) of the title compound as yellow crystals, mp 150°-153° C.; 1H NMR (DMSO-d6) δ10.65 (s, 1H), 8.22 (d, J=9.2, 2H), 7.86 (d, J=9.2, 2H), 7.04 (ddd, J=9.6, J=8.4, J=1.6, 1H), 6.94 (dt, J=7.2, J=1.2, 1H), 6.65-6.61 (m, 2H), 5.80 (bs, 1H), 4.02 (s, 2H); 13C NMR (DMSO-d6) δ170.06, 150.91 (d, J=236), 144.99, 142.23, 136.31 (d, J=11.3), 124.98, 124.75 (d, J=3.5), 118.90, 116.36 (d, J=6.4), 114.44 (d, J=17.6), 112.17 (d, J=14.0), 46.79; MS (El, m/z) 289 (M+). Anal. Calcd for C14H12N3 O3F: C, 58.12; H, 4.18; N, 14.53. Found: C, 58.04; H, 4.20; N, 14.36.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with CH2Cl2 (200 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. additiona small amount of silica gel was added to the CH2 Cl2 solution
  6. concentrationthe mixture was concentrated
  7. customPurification by chromatography
  8. washeluting with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-e380ef7e63d2463da763b0ea660b812f
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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