Ethyl Acetate → HCID 86592334, compound

HRID 1269566Notes

Reaction equation

HRID 1269566 reaction equation
[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)=[C:14]([Cl:29])[C:13]=1[CH2:30][CH3:31])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OC(=O)C)C>C(O)C>[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=2)=[C:14]([Cl:29])[C:13]=1[CH2:30][CH3:31])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86592335HCID 86592335, compound

Product 1

HCID 86592334HCID 86592334, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl(3,5-dichloro-4-[4-nitrophenoxy]phenyl) cinnamate (0.65 g), tindichloride dihydrate (1.0 g), ethylacetate (25 mL) and ethanol (25 mL) was heated at reflux for one hour. The reaction mixture was concentrated and the residue partioned beetween diethyl ether and sodium hydroxide (1 N). After purification on column (silica gel, ethyl acetate/petrolium ether, 3:7), 0.52 g of ethyl(3,5-dichloro-4-[4-aminophenoxy]phenyl) cinnamate was obtained.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. concentrationThe reaction mixture was concentrated
  4. customAfter purification on column (silica gel, ethyl acetate/petrolium ether, 3:7)

Sources & evidence

ORD record
ord-9b5fd81598624f37962554fd444bf001
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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