HCID 67168067, compound → HCID 58268612, compound

HRID 1517572Notes

Reaction equation

HRID 1517572 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:6]([N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[C:13]([CH3:18])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:3]>ClCCl>[CH3:3][N:2]([CH2:4][C:5]1[C:6]([N:11]2[CH:15]=[C:14]([CH:16]=[O:17])[C:13]([CH3:18])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

3

Reactant 1

HCID 67168067HCID 67168067, compound

Product 1

HCID 58268612HCID 58268612, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3,3-Triacetoxy-3-iodophthalide (0.553 g, 1.3 mmol) is added to a solution of [1-[3-(dimethylaminomethyl)-2-pyridyl]-3-methyl-pyrazol-4-yl]methanol (0.146 g, 0.59 mmol) in dichloromethane (4 mL) at room temperature. After one hour the reaction is quenched by addition of 2N sodium carbonate solution and the compound is extracted in dichloromethane. The organic layer is separated, dried over magnesium sulfate and the solvent evaporated in vacuo to afford 126 mg of 1-[3-(dimethylaminomethyl)-2-pyridyl]-3-methyl-pyrazole-4-carbaldehyde that is used with no further purification. MS (m/z): 245 (M+1).

Workup

  1. customAfter one hour the reaction is quenched by addition of 2N sodium carbonate solution
  2. extractionthe compound is extracted in dichloromethane
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-ddddbb2d91ed4839aef2e13b4222fbe8
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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