Sodium Hydroxide → 3,4,5-Trimethoxy-N-methylaniline

HRID 1290791Notes

Reaction equation

HRID 1290791 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14](=O)OCC)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH3:14][NH:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 9517640HCID 9517640, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 144819853,4,5-Trimethoxy-N-methylaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 3,4,5-trimethoxyphenylcarbamate (6.0 g) in tetrahydrofuran (150 ml) was added a 1M solution of lithium aluminum hydride in tetrahydrofuran (23.5 ml) dropwise. The mixture was stirred at room temperature for 1 hour, then refluxed for 1 hour. The product was cooled and an excess of 1M sodium hydroxide added dropwise. The precipitate was filtered off, and the filtrate partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, and solvent removed under reduced pressure. The residue was redissolved in ethyl acetate and washed with 2M hydrochloric acid. The aqueous layer was washed with ethyl acetate, then basified with 1M sodium hydroxide, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and solvent removed under reduced pressure, to give N-methyl-3,4,5-trimethoxyaniline.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe product was cooled
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate partitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried over magnesium sulfate, and solvent
  6. customremoved under reduced pressure
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. washwashed with 2M hydrochloric acid
  9. washThe aqueous layer was washed with ethyl acetate
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic layer was dried over magnesium sulfate, and solvent
  12. customremoved under reduced pressure

Sources & evidence

ORD record
ord-aa72ac82c5494db5a6050cd7b1d64a8c
Source dataset
uspto-grants-1998_05
Patent number
US05753663

Reaction notes

Loading…