HCID 14576224, compound → HCID 14576225, compound

HRID 232157Notes

Reaction equation

HRID 232157 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:10]([CH2:17][OH:18])=[N:9]2)=[CH:4][CH:3]=1>[O-2].[Mn+4].[O-2].C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:10]([CH:17]=[O:18])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 14576224HCID 14576224, compound

Product 1

HCID 14576225HCID 14576225, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A toluene (150 ml) solution of the compound of Example 77 (3.0 g) was treated with activated manganese (IV) oxide (9.0 g) and azeotropically distilled during 30 minutes. The hot suspension was filtered and the filtrate evaporated to yield pure title compound (1.99 g). A repeat reaction provided 2.0 g. Crystallization of the combined product from acetonitrile gave 3.80 g, m.p. 120°-121° C.

Workup

  1. distillationazeotropically distilled during 30 minutes
  2. filtrationThe hot suspension was filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-50fadb6541b44c47a5ff3255cbc70dec
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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