Acetic Acid → HCID 15516381, compound

HRID 1266184Notes

Reaction equation

HRID 1266184 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.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].C(O)(=O)C.[BH4-].[Na+]>CO>[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:6][C:5]2[CH:7]=[CH:8][C:9]3[O:10][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 843101,3-Benzodioxol-5-amineHCID 4311764Sodium borohydride

Product 1

HCID 15516381HCID 15516381, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4-methylenedioxyaniline (10 mmol) and 4-nitrobenzaldehyde (10 mmol) in methanol is stirred at ambient temperature for 18 hours. The precipitate obtained is filtered off and washed and then dissolved in tetrahydrofuran. After the addition of acetic acid and sodium borohydride (25 mmol), the reaction mixture is stirred at ambient temperature for 1 hour, then the solvent is evaporated off and the crude residue is purified by chromatography on silica using dichloromethane as eluant.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed
  4. dissolutiondissolved in tetrahydrofuran
  5. customthe solvent is evaporated off
  6. customthe crude residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-ba02b3f9cd7846c8aa14ebdf413aa64a
Source dataset
uspto-grants-2003_04
Patent number
US06548515B1

Reaction notes

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