Ethanol → HCID 19430576, compound

HRID 1077979Notes

Reaction equation

HRID 1077979 reaction equation
[N+:1]([C:4]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:5]=1[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([O-])=O.C(O)C.O>C(O)(=O)C>[NH2:1][C:4]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:5]=1[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 19430535HCID 19430535, compound

Product 1

HCID 19430576HCID 19430576, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-(2-nitro-4-bromophenoxy)benzoic acid (0.6 g, 0.0018 mol) iron powder (0.69 g 0.012 mol), ethanol (46 mL), water (41 mL), and acetic acid (4.6 mL) was heated to 75° C. for 30 minutes. The mixture was filtered and the solvents evaporated to give the crude product which was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid) to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ8.09 (dd, 1H), 7.45-7.50 (m, 1H), 7.16-7.26 (m, 1H), 6.99 (d, 1H), 6.84-6.89 (m, 2H), 6.78 (d, 1H), 5.35 (br s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents evaporated
  3. customto give the crude product which
  4. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)

Sources & evidence

ORD record
ord-41566914fdf345e9aa3e35848d43a266
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

Loading…