Trimethyl orthobeznoate → 1-Acetyl-3-(1-methoxy-1-phenyl-methylidene)-5-nitro-2-indolinone

HRID 24797

Reaction equation

HRID 24797 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:16])(=[O:3])[CH3:2].[CH3:17][O:18][C:19](OC)(OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OC(=O)C)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:19]([O:18][CH3:17])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]1=[O:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 28393291-Acetyl-5-nitroindolin-2-one

Product 1

HCID 541401551-Acetyl-3-(1-methoxy-1-phenyl-methylidene)-5-nitro-2-indolinone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

30.0 g (0.137 mol) of 1-acetyl-5-nitro-2-indolinone are dissolved in 200 ml of acetic anhydride and after the addition of 50.0 g (0.274 mol) of trimethyl orthobenzoate stirred for 3 hours at 100° C. After cooling it is evaporated down to half the quantity, diluted with ether/petroleum ether, the precipitate is suction filtered and dried.

Workup

  1. temperatureAfter cooling it
  2. customis evaporated down to half the quantity
  3. additiondiluted with ether/petroleum ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-9462538d776349bebad5c84c86b36c45
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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