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

HRID 896418Notes

Reaction equation

HRID 896418 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-a2723bf0468b4d7c8259cd86b9a90966
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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