Sodium Hydroxide → HCID 15291669, compound

HRID 2399297Notes

Reaction equation

HRID 2399297 reaction equation
[NH2:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15291668HCID 15291668, compound

Product 1

HCID 15291669HCID 15291669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-amino-4-trifluoromethylphenoxy)benzoate (11.68 g, 0.0375 mol) was mixed in tetrahydrofuran (175 ml) and sodium hydroxide (77 ml) at 40° C. for sixteen hours. The solvents were evaporated and water added to the residue. 3N hydrochloric acid was then added to the mixture until the maximum precipitate was given. The aqueous mixture was extracted with ethyl acetate (3×) and the organic phase dried over MgSO4 and evaporated. The residue was flash chromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide) to give the title compound. 1H NMR (250 MHz, CD3OD) δ7.90 (dd, 1H), 7.5 (tt, 1H), 7.2 (tt, 1H), 7.09 (d, 1H), 6.95 (dd, 1H), 6.85 (dd, 1H), 6.75 (d, 1H).

Workup

  1. customThe solvents were evaporated
  2. additionwater added to the residue
  3. addition3N hydrochloric acid was then added to the mixture until the maximum precipitate
  4. extractionThe aqueous mixture was extracted with ethyl acetate (3×)
  5. dry with materialthe organic phase dried over MgSO4
  6. customevaporated
  7. customchromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-59da83c932ba40db862b9925df6a8150
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

Loading…