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

HRID 902143Notes

Reaction equation

HRID 902143 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-dd8af04ea5ca49a987341c1b80ca3883
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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