Silicon carbide → 2,4,5-Trimethoxyaniline

HRID 1461970Notes

Reaction equation

HRID 1461970 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[N+:13]([O-])=O.[C-]#[Si+].[OH-].[Na+]>Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[NH2:13]

Participants

5

Reactant 3

HCID 9863Silicon carbideHCID 14798Sodium HydroxideHCID 8224151,2,4-Trimethoxy-5-nitrobenzene

Product 1

HCID 124101382,4,5-Trimethoxyaniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into a 500 cm3 flask, provided with a cooling device, were added successively 21.3 g (0.1 mole) of 2,4,5-trimethoxy nitrobenzene, 80 g of chemically pure stannous chloride for mirror making, 100 cm3 of a hydrochloric acid solution (d=1.18) and carborundum. The mixture was brought to boiling under reflux for 1 h. After cooling, a caustic soda solution was added until the precipitate dissolved. The solution obtained was extracted with methylene chloride. The organic extracts were dried over sodium sulfate then evaporated under reduced pressure. The residue obtained was crystallized in ethanol.

Workup

  1. customInto a 500 cm3 flask, provided with a cooling device
  2. temperatureunder reflux for 1 h
  3. temperatureAfter cooling
  4. dissolutiondissolved
  5. customThe solution obtained
  6. extractionwas extracted with methylene chloride
  7. dry with materialThe organic extracts were dried over sodium sulfate
  8. customthen evaporated under reduced pressure
  9. customThe residue obtained
  10. customwas crystallized in ethanol

Sources & evidence

ORD record
ord-e9ae033fe5b149b3b0dab163eb355f79
Source dataset
uspto-grants-1984_07
Patent number
US04457875

Reaction notes

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