Pyridinium chloride → HCID 20494731, compound

HRID 1075305Notes

Reaction equation

HRID 1075305 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([CH3:19])[CH:13]=[CH:14][C:15]=2[O:17]C)[C:10](=[O:20])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([CH3:19])[CH:13]=[CH:14][C:15]=2[OH:17])[C:10](=[O:20])[C:9]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 20494733HCID 20494733, compound

Product 1

HCID 20494731HCID 20494731, compoundYield 25.5%

Procedure

15.46 g of 1-benzyl-4-methyl-7-methoxy-2,3-indoledione and 74 g of pyridine hydrochloride were heated to 200° C. for 2.5 hours. The mixture was partitioned between methylene chloride and aqueous dimethyl sulfoxide. The organic layer was separated and evaporated to give 3.75 g of crude 1-benzyl-4-methyl-7-hydroxy-2,3-indoledione in the form of a red solid having a melting point of 255°-262° C.

Workup

  1. customThe mixture was partitioned between methylene chloride and aqueous dimethyl sulfoxide
  2. customThe organic layer was separated
  3. customevaporated

Sources & evidence

ORD record
ord-9fa376ba11e14259be5503e01e5fa1b7
Source dataset
uspto-grants-1983_07
Patent number
US04395559

Reaction notes

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