Pyridine → 1H-Indole-4-carbaldehyde O-methyl-oxime

HRID 2236434Notes

Reaction equation

HRID 2236434 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=O)[C:4]=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:5]1[C:4]2[CH:3]=[CH:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 333703Indole-4-carboxaldehydeHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 722508571H-Indole-4-carbaldehyde O-methyl-oximeYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an amount of 1H-Indole-4-carbaldehyde (50 mg, 0.34 mmol) is added pyridine (10 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 2 mL of water is added. After the solvents were evaporated, the residue is dissolved 2 mL of anhydrous ether, washed successively with 2 mL of aqueous sodium bicarbonate, 2 mL of sodium bisulfite, and 2 mL of brine. Dried over magnesium sulfate, evaporated to give a white solid (35 mg). MS (ESI) m/z 175.2 (M+1)

Workup

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

Sources & evidence

ORD record
ord-54adcbfd228945d2bd7271ff220298d8
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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