Formic Acid → 1,3-Benzodioxol-5-amine, N-methyl-

HRID 1266183Notes

Reaction equation

HRID 1266183 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[CH:19](O)=O>O.CCOCC>[CH3:19][NH:6][C:5]1[CH:7]=[CH:8][C:9]2[O:10][CH2:1][O:2][C:3]=2[CH:4]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 843101,3-Benzodioxol-5-amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 106069191,3-Benzodioxol-5-amine, N-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,4-methylenedioxyaniline (10 mmol) in formic acid (36 ml) is heated at reflux for 1 hour. After the removal of excess formic acid, the residue obtained is diluted with water and then extracted with dichloromethane. The combined organic phases are evaporated. The residue obtained is dissolved in ether, then lithium aluminium hydride (42 mmol) is added at 10° C., in small portions. After stirring the mixture at ambient temperature for 3 hours, water and 10% sodium hydroxide solution are added and the mixture is then filtered over Celite. The filtrate is dried and evaporated and the residue obtained is purified by chromatography on silica, using dichloromethane as eluant, to yield the expected product in the form of an oil.

Workup

  1. temperatureat reflux for 1 hour
  2. customAfter the removal of excess formic acid
  3. customthe residue obtained
  4. extractionextracted with dichloromethane
  5. customThe combined organic phases are evaporated
  6. customThe residue obtained
  7. filtrationthe mixture is then filtered over Celite
  8. customThe filtrate is dried
  9. customevaporated
  10. customthe residue obtained
  11. customis purified by chromatography on silica

Sources & evidence

ORD record
ord-812a290eea024b6d9625f963c132b1f0
Source dataset
uspto-grants-2003_04
Patent number
US06548515B1

Reaction notes

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