Methanol → HCID 87829163, compound

HRID 1269565Notes

Reaction equation

HRID 1269565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](CC(O)=O)[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:16]([O-])=O)[CH:10]=1.CO.[C:26](=O)([O-])O.[Na+].[C:31]([O:34]CC)(=[O:33])[CH3:32]>S(Cl)(Cl)=O>[C:31]([O:34][C:4]1[CH:5]=[C:6]([Cl:19])[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=2)=[C:2]([Cl:1])[C:3]=1[CH3:26])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18448755HCID 18448755, compound

Product 1

HCID 87829163HCID 87829163, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Procedure

3,5-Dichloro-4-(4-amino-3-nitrophenoxy)phenylacetic acid (50 mg), methanol (20 mL) and thionyl chloride (2 drops) was heated at reflux for two hours. After cooling down to room temperature, the reaction mixture was partioned between an aqueous solution of sodium hydrogencarbonate (saturated) and ethyl acetate. The organic phase was washed with brine and concentrated. This gave 45 mg of methyl(3,5-dichloro-4-(4-amino-3-nitro-phenoxy)phenyl) acetate which was reduced using the method described in Example 1(f), to give 40 mg of methyl(3,5-dichloro-4-(3,4-diaminophenoxy)phenyl) acetate.

Workup

  1. temperatureat reflux for two hours
  2. washThe organic phase was washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-54b417ab2eeb47d39c1b658cf3e0763b
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

Loading…