Ethyl orthoformate → 1-(3-Chlorophenyl)-3-(ethoxymethylene)-2(1H,3H)-indolone

HRID 1723565Notes

Reaction equation

HRID 1723565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.[CH:18](OCC)(OCC)[O:19][CH2:20][CH3:21].C([O-])([O-])[O-]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[CH:18][O:19][CH2:20][CH3:21])[C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 112995301-(3-Chlorophenyl)-indolin-2-oneHCID 21585117Orthoformate

Product 1

HCID 537126431-(3-Chlorophenyl)-3-(ethoxymethylene)-2(1H,3H)-indoloneYield 140.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(3-Chlorophenyl)-2(1H,3H)-indolone (2.4 g, 0.01 mole) and triethyl orthoformate (8.3 ml, 0.05 mole) were combined and heated at 150°±10° for 18 hours. An additional 20 ml of the orthoformate were added and heating continued 2 hours. The reaction mixture was cooled to 25°, diluted with ether, washed with H2O and then brine, dried over MgSO4, concentrated in vacuo to oily solids, and triturated with pentane to yield solids (4.2 g). The solids were chromatographed on silica gel (7.5×15 cm) with 4:1 hexane:ethyl acetate as eluant to yield purified title product, 0.5 g; m.p. 132°-134°; m/e 310/299.

Workup

  1. temperatureheated at 150°±10° for 18 hours
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled to 25°
  4. washwashed with H2O
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated in vacuo to oily solids
  7. customtriturated with pentane

Sources & evidence

ORD record
ord-9921661696c64a11afbb267a74da802d
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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