Benzene, (triethoxymethyl)- → 1-Acetyl-3-(1-ethoxy-1-phenylmethylidene)-5,6-dimethoxy-2-indolinone

HRID 1007382Notes

Reaction equation

HRID 1007382 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][C:5]1=[O:17])(=[O:3])[CH3:2].[CH3:18][CH2:19][O:20][C:21](OCC)(OCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OC(=O)C)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6](=[C:21]([O:20][CH2:19][CH3:18])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]1=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 74268Benzene, (triethoxymethyl)-HCID 226685441-Acetyl-5,6-dimethoxy-2-indolinone

Product 1

HCID 695643221-Acetyl-3-(1-ethoxy-1-phenylmethylidene)-5,6-dimethoxy-2-indolinone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

10.0 g of 1-acetyl-5,6-dimethoxy-2-indolinone, 29.2 ml of triethyl orthobenzoate and 100 ml of acetic anhydride are stirred for 48 hours at 120° C. The solvent is eliminated and the residue evaporated with toluene, combined with ether and the precipitate formed (starting compounds is suction filtered. The filtrate is concentrated by evaporation and separated through a silica gel column with toluene, then with toluene/ethyl acetate (10:1). The product is triturated with ether, suction filtered and dried in vacuo at 100° C.

Workup

  1. customthe residue evaporated with toluene
  2. customthe precipitate formed (
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated by evaporation
  5. customseparated through a silica gel column with toluene
  6. customThe product is triturated with ether, suction
  7. filtrationfiltered
  8. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-a702140750b24dcc85f451cc428b390a
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Reaction notes

Loading…