Methyl 3-(2-methyl-6-nitrophenyl)propenoate → methyl 4-methyl-1H-indole-2-carboxylate

HRID 511853Notes

Reaction equation

HRID 511853 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14]>C(OP(OCC)OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[NH:8]2

Participants

3

Reactant 1

HCID 67291648Methyl 3-(2-methyl-6-nitrophenyl)propenoate

Product 1

HCID 4714967methyl 4-methyl-1H-indole-2-carboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

Methyl 3-(2-methyl-6-nitrophenyl)propenoate (0.24 g, 1.1 mmol) was dissolved in triethylphosphite (1 mL) and heated under reflux for 20 h. The solvent was removed in vacuo and the crude product was purified by silica gel chromatography (EtOAc:hexane=8:92) to give 0.15 g (71% yield) of the title compound as a pale yellow solid:

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 h
  3. customThe solvent was removed in vacuo
  4. customthe crude product was purified by silica gel chromatography (EtOAc:hexane=8:92)

Sources & evidence

ORD record
ord-9c718672990641d1aa6fc2011cfb88db
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

Loading…