Water → (E)-3-[2-(2-nitrophenyl)vinyl]-1H-indazole

HRID 1821316Notes

Reaction equation

HRID 1821316 reaction equation
[I-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.[N+:31]([C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=O)([O-:33])=[O:32].C(=O)([O-])[O-].[K+].[K+].O>CO>[N+:31]([C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1/[CH:36]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][N:3]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 111012-NitrobenzaldehydeHCID 11430Potassium CarbonateHCID 178506551HCID 178506551, compound

Product 1

HCID 68999900(E)-3-[2-(2-nitrophenyl)vinyl]-1H-indazoleYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1H-indazol-3-ylmethyl)triphenylphosphonium iodide (3.12 g, 6.00 mmol) was dissolved in methanol (50 mL) and the solution was added with o-nitrobenzaldehyde (1.00 g, 6.60 mmol) and potassium carbonate (2.82 g, 20.40 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with water. The precipitated solid was collected by filtration and then dried. The obtained solid was triturated in methanol to obtain Compound 1 (1.05 g, 76%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried
  3. customThe obtained solid was triturated in methanol

Sources & evidence

ORD record
ord-3fd7caccda994d3c8ca8ff18541cc026
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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