Formaldehyde → HCID 66817460, compound

HRID 1755010Notes

Reaction equation

HRID 1755010 reaction equation
[CH3:1][O-].[Na+].[I:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([CH3:12])[C:6]=1[CH3:13].C=O.[BH4-].[Na+].[OH-].[Na+]>CO>[I:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][CH3:1])=[C:7]([CH3:12])[C:6]=1[CH3:13]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 140402864-Iodo-2,3-dimethylbenzenamine

Product 1

HCID 66817460HCID 66817460, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methoxide in methanol (0.694 ml, 6.07 mmol) was added to a solution of 4-iodo-2,3-dimethyl-aniline (500 mg, 2.02 mmol) and paraformaldehyde (121 mg, 4.05 mmol) in methanol (8.0 ml), and the mixture was stirred at room temperature for 17 hours. Sodium borohydride (153 mg, 4.05 mmol) was further added, and the mixture was stirred at room temperature for four hours. A 1 N aqueous NaOH solution was added to the reaction mixture, followed by extraction with dichloromethane. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-iodo-N,2,3-trimethyl-aniline (146 mg, 88%).

Workup

  1. stirringthe mixture was stirred at room temperature for four hours
  2. extractionfollowed by extraction with dichloromethane
  3. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-61d8a7641c2e4c4ea3e245f9bba8dc33
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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