2-Propenoic acid, 2-azido-3-(4-methoxyphenyl)-, methyl ester → Methyl-6-methoxy-2-indolecarboxylate

HRID 2293762Notes

Reaction equation

HRID 2293762 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH:7]=[C:8]([N:13]=[N+]=[N-])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:17]=[C:16]2[C:6]([CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[NH:13]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 43674462-Propenoic acid, 2-azido-3-(4-methoxyphenyl)-, methyl ester

Product 1

HCID 688173Methyl-6-methoxy-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (185 ml) is added to methyl 4-methoxy-α-azidocinnamate (PREPARATION 61, 7.73 g) and the reaction is brought to reflux and maintained at reflux for 3 hr. Then the reaction is concentrated under reduced pressure and triturated with hexane. The solids are filtered and dried under reduced pressure to give the title indole, HRMS Calcd. for C11H11NO3 : 205.0739, found: 205.0736; NMR (300 MHz, CDCl3) 8.75, 7.47, 7.11, 6.76-6.73, 3.86, 3.79 δ.

Workup

  1. temperatureto reflux
  2. temperaturemaintained
  3. temperatureat reflux for 3 hr
  4. concentrationThen the reaction is concentrated under reduced pressure
  5. customtriturated with hexane
  6. filtrationThe solids are filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd14d2b86da343d8ad811fad65f4ffdc
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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