Pyridine → 1H-Indole-6-carbaldehyde O-methyl-oxime

HRID 2236430Notes

Reaction equation

HRID 2236430 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=O)[CH:8]=2)[CH:3]=[CH:2]1.N1C=CC=CC=1.Cl.[O:19]([NH2:21])[CH3:20]>O>[CH3:20][O:19][N:21]=[CH:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 722508601H-Indole-6-carbaldehyde O-methyl-oximeYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 1H-Indole-6-carbaldehyde (50 mg, 0.34 mmol) is added to pyridine (2.0 ml) at room temperature, followed by addition of methoxylamine hydrogen chloride (31.6 mg, 0.38 mmol). The mixture is stirred at ambient temperature for 24 h, and 10 mL of water is added. After the solvents were evaporated, the residue is dissolved 10 mL of anhydrous ether, washed successively with 10 mL of aqueous sodium bicarbonate, 10 mL of sodium bisulfite, and 10 mL of brine. Dried over magnesium sulfate, evaporated to give a white solid (49 mg, 0.281 mmol). MS (ESI) m/z 176.3 (M+1)

Workup

  1. customAfter the solvents were evaporated
  2. dissolutionthe residue is dissolved 10 mL of anhydrous ether
  3. washwashed successively with 10 mL of aqueous sodium bicarbonate, 10 mL of sodium bisulfite, and 10 mL of brine
  4. dry with materialDried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9755bd7b0d8e47f39496ab019f24d438
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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