Sodium Hydroxide → HCID 15291669, compound

HRID 2399275Notes

Reaction equation

HRID 2399275 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

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-(2-amino-4-trifluoromethylphenoxy)benzoate (19.2 g, 0.062 mol) and 2N sodium hydroxide (65 mL, 0.13 mol) in tetrahydrofuran (100 mL) was warmed to 50° C. while stirring under argon for 3 h. The tetrahydrofuran was evaporated, and the aqueous solution was acidified with dilute HCl, extracted with ethyl acetate, dried over anhydrous MgSO4, filtered and evaporated. The crude product was recrystallized from EtOAc/hexane to give the title compound as a white crystalline solid. 1H NMR (250 MHz, CD3OD) δ7.91 (d, 1H), 7.50 (dd, 1H), 7.22 (dd, 1H), 7.11 (d, 1H), 6.97 (d, 1H), 6.86 (d, 1H), 6.78 (d, 1H).

Workup

  1. customThe tetrahydrofuran was evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-8338c3511a614701b6e13576f66b5d5f
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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