Pyridine → 3-Hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde O-methyl-oxime

HRID 2236436Notes

Reaction equation

HRID 2236436 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:5]=O.N1C=CC=CC=1.Cl.[O:25]([NH2:27])[CH3:26]>O>[CH3:26][O:25][N:27]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 867611093-Hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

Product 1

HCID 722507613-Hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde O-methyl-oximeYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 3-hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (150 mg, 0.64 mmol) is added pyridine (3.5 ml) at room temperature, followed by addition of methoxylamine hydrogen chloride (58.2 mg, 0.70 mmol). The mixture is stirred at ambient temperature for 24 h, and 4 mL of water is added. After the solvents were evaporated, the residue is dissolved 8 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 yellow solid (100 mg). MS (ESI) m/z 265.8 (M+1)

Workup

  1. customAfter the solvents were evaporated
  2. dissolutionthe residue is dissolved 8 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-d9dca58f60b84c6a9aed32494d028d44
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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