2-Fluoroaniline → HCID 18929196, compound

HRID 1599842Notes

Reaction equation

HRID 1599842 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:4].[F:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>CN(C=O)C>[F:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 4625969HCID 4625969, compound

Product 1

HCID 18929196HCID 18929196, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-((bromoacetyl)amino)benzoate (1.0 g, 3.5 mmol) and 2-fluoroaniline (1.0 g, 0.87 mL, 9 mmol) in anhydrous DMF (30 mL) was heated to 90°-100° C. overnight with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then extracted with 3×50 mL of ethyl acetate. The layers were separated, and then the organic layer was dried (MgSO4), filtered and then concentrated. Purification by chromatography, eluting with hexane-ethyl acetate (3:1), afforded 0.75 g (68%) of the title compound, mp 79°-81° C.: 1H NMR (DMSO-d6) δ11.41 (s, 1H), 8.59 (dd, J=8.4, J=0.8, 1H), 7.91 (dd, J=8.0, J=1.2, 1H), 7.61 (ddd, J=8.8, J=7.6, J=1.6, 1H), 7.17 (ddd, J=8.0, J=7.6, J=1.2, 1H), 7.08 (ddd, J=9.2, J=8.0, J=1.2, 1H), 6.93 (ddd, J=8.8, J=8.0, J=1.2, 1H), 6.63-6.54 (m, 2H), 6.34 (t, J=5.6, 1H), 4.18 (q, J=7.2, 2H), 3.90 (s, J=5.6, 1H), 1.21 (t, J=7.2, 3H); 13C NMR (DMSO-d6) δ170.08, 166.60, 151.12 (d, J=237), 139.59, 135.99 (d, J=11.3), 134.19, 130.67, 124.76 (d, J=3.1), 123.04, 120.08, 117.07 (d, J=6.9), 116.37, 114.49 (d, J=18.2), 112.12 (d, J=3.0), 61.13, 48.31, 13.86; MS (EI, m/z) 316 (M+). Anal. Calcd for C17H1 7N2O3F: C, 64.54; H, 5.42; N, 8.86. Found: C, 64.18; H, 5.37; N, 8.83.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography
  8. washeluting with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ff9c201016a2409f97f6224aae37d6e5
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

Loading…