Methyl(Z)-2-azido-3-(4-benzyloxy-3-nitrophenyl)acrylate → Methyl 6-benzyloxy-5-nitro-indole-2-carboxylate

HRID 2224591Notes

Reaction equation

HRID 2224591 reaction equation
[N:1](/[C:4](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([N+:24]([O-:26])=[O:25])[CH:11]=1)/[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-]>C1(C)C(C)=CC=CC=1>[CH2:17]([O:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[NH:1]2)=[CH:11][C:12]=1[N+:24]([O-:26])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 86598196Methyl(Z)-2-azido-3-(4-benzyloxy-3-nitrophenyl)acrylate

Product 1

HCID 16110225Methyl 6-benzyloxy-5-nitro-indole-2-carboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred solution of 200 ml of boiling xylene 4.93 g ((13.9 mmol) of methyl (Z)-2-azido-3-(4-benzyloxy-3-nitrophenyl)acrylate is added in small portions. After completion of the addition the reaction mixture is refluxed until the gas formation is over (about 0.5 h), then cooled to room temperature, the precipitated product is filtered off and washed with n-hexane to yield 0.67 g (15%) of the title compound. Mp.: 184-187° C. (xylene).

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. temperatureis refluxed until the gas formation
  3. customis over (about 0.5 h)
  4. filtrationthe precipitated product is filtered off
  5. washwashed with n-hexane

Sources & evidence

ORD record
ord-7b9e5d17aa4049c29462f4f0b4999f36
Source dataset
uspto-grants-2008_05
Patent number
US07378431B2

Reaction notes

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