Sodium Hydroxide → HCID 85728081, compound

HRID 361297Notes

Reaction equation

HRID 361297 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.Cl.[CH3:16][NH:17][OH:18].[OH-].[Na+]>C(O)C.O>[CH3:16][N+:17]([O-:18])=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 750062,3,4-TrimethoxybenzaldehydeHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 85728081HCID 85728081, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 9.97 g (50.9 mmol) of 2,3,4-trimethoxybenzaldehyde and 4.43 g (53.1 mmol) of N-methylhydroxylamine hydrochloride in 100 mL of ethanol was added a solution of 2.05 g (51.3 mmol) of sodium hydroxide in 15 mL of water. The mixture was stirred at room temperature for 22 h and evaporated in vacuo to remove the bulk of the solvent. The residual solid was taken up in 150 mL of dichloromethane, washed with 50 mL of water and dried over MgSO4. Removal of the solvent afforded 11.31 g of N-methyl-C-(2,3,4-trimethoxyphenyl)nitrone as a white solid. 1H-NMR (CDCl3) d 3.85-3.95 (9H), 6.75 (d, 1H), 7.65 (s, 1H), 9.1 (d, 1H).

Workup

  1. customevaporated in vacuo
  2. customto remove the bulk of the solvent
  3. washwashed with 50 mL of water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-d8f72326ee744defb68714492fa82820
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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