HCID 19430555, compound → HCID 19430557, compound

HRID 1077980Notes

Reaction equation

HRID 1077980 reaction equation
[N+:1]([C:4]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-])=O>C(O)(=O)C.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:1][C:4]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 19430555HCID 19430555, compound

Product 1

HCID 19430557HCID 19430557, compound

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of methyl 2-(2-nitro-4,5-dichlorophenoxy)benzoate (2 g, 5.86 mmol) in acetic acid (50 mL) was treated with 20% aqueous titanium trichloride (22 mL, 36 mmol). The solvent was evaporated, and the aqueous residue was made basic with aqueous sodium hydroxide. The crude product was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and evaporated. Flash chromatography (silica gel, ethyl acetate/hexane), followed by recrystallization from-ethyl acetate/hexane gave the title compound. 1H NMR (400 MHz, CDCl3) δ7.90 (dd, 1H), 7.46-7.50 (m, 1H), 7.18-7.26 (m, 1H), 6.93 (dd, 1H), 6.89 (s, 1H), 6.83 (s, 1H), 4.08 (br s, 2H), 3.87 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. extractionThe crude product was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customFlash chromatography (silica gel, ethyl acetate/hexane), followed by recrystallization from-ethyl acetate/hexane

Sources & evidence

ORD record
ord-7811c39294ac4ab6b6922ffb8bf3dcd8
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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