O-Xylene → HCID 22350183, compound

HRID 2223200Notes

Reaction equation

HRID 2223200 reaction equation
C1(C)C(C)=CC=CC=1.[N:9](/[C:12](=[CH:17]\[C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)/[C:13]([O:15][CH3:16])=[O:14])=[N+]=[N-]>>[NH:9]1[C:19]2[C:18](=[CH:26][CH:25]=[C:24]3[C:20]=2[CH:21]=[CH:22][NH:23]3)[CH:17]=[C:12]1[C:13]([O:15][CH3:16])=[O:14]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 86598195HCID 86598195, compound

Product 1

HCID 22350183HCID 22350183, compoundYield 62%

Procedure

To a boiling solution of 36 ml of xylene 1.09 g (4.5 mmol) of methyl (Z)-2-azido-3-(1H-indole-5-yl)acrylate is added in small portions. The reaction mixture is refluxed till the end of the nitrogen gas formation, then concentrated and the residue is crystallized with hexane, the product is filtered and washed with hexane to yield 0.6 g (62%) of the title compound. Mp.: 183-184° C. (hexane).

Workup

  1. temperatureThe reaction mixture is refluxed till the end of the nitrogen gas formation
  2. concentrationconcentrated
  3. customthe residue is crystallized with hexane
  4. filtrationthe product is filtered
  5. washwashed with hexane

Sources & evidence

ORD record
ord-ca81640abbdb44419fad23ce1be75c15
Source dataset
uspto-grants-2008_05
Patent number
US07375116B2

Reaction notes

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