4-Fluoro-3-nitrobenzoic acid → 3-Nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino)benzoic acid

HRID 2111800Notes

Reaction equation

HRID 2111800 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.F[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[N+:28]([O-:30])=[O:29]>C(O)C>[N+:28]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:19]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:17][CH:16]=1)[C:23]([OH:25])=[O:24])([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 690679354-[2-(Pyridin-2-yloxy)ethoxy]aniline

Product 1

HCID 690675383-Nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[2-(Pyridin-2-yloxy)ethoxy]aniline (4.50 g, 19.50 mmol) and 4-fluoro-3-nitrobenzoic acid (3.60 g, 19.50 mmol) were dissolved in ethanol (100 mL) and refluxed under nitrogen for 18 h. The reaction mixture was filtered and washed with cold ethanol (×2) to give 3-nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino) benzoic acid as a reddish orange solid. 1H NMR (d6-DMSO, 400 MHz): δ 9.77 (brs, 1H), 8.64 (d, J=2.4 Hz, 1H), 8.18 (ddd, J=5.2, 2.0, 0.8 Hz, 1H), 7.88 (dd, J=9.6, 2.0 Hz, 1H), 7.73 (ddd, J=8.8, 6.8, 2.0 Hz, 1H), 7.29 (ddd, J=6.4, 3.2, 3.2 Hz, 1H), 7.08 (ddd, J=5.6, 3.2, 3.2 Hz, 1H), 7.01 (ddd, J=7.4, 5.2, 1.2 Hz, 1H), 6.97 (d, J=9.2 Hz, 1H), 6.87 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 4.60 (m, 2H), 4.37 (m, 2H), 4.15 (m, 2H). MS(ES+): m/z 396.45 (100) [MH+].

Workup

  1. temperaturerefluxed under nitrogen for 18 h
  2. filtrationThe reaction mixture was filtered
  3. washwashed with cold ethanol (×2)

Sources & evidence

ORD record
ord-e8884cefc9474fa08724a263f09e98fc
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

Loading…