HCID 57436585, compound → HCID 57436586, compound

HRID 730935Notes

Reaction equation

HRID 730935 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[O:19][CH3:20])[CH:7]=[CH:8][CH:9]=1>CO.O1CCCC1.[Pd]>[ClH:1].[ClH:1].[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[C:14]([CH:13]=[CH:12][C:11]=2[O:19][CH3:20])[NH2:16])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 57436585HCID 57436585, compound

Product 1

HCID 57436586HCID 57436586, compoundYield 149.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-aminomethylphenyl)-4-nitroanisole hydrochloride (1.26 g, 4.2 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) under nitrogen was added palladium on carbon (10% by weight, 200 mgs, 15 wt. %). The solution was purged with hydrogen and stirred under hydrogen for 24 hours. The reaction was purged with nitrogen and the catalyst was removed by filtration. Solvent was removed in vacuo and the residue was redissolved in dichloromethane (10 mL) and hydrochloride acid was added (4.0 M solution in dioxane, 1.5 equiv., 1.57 mL). The solution was stirred for 1 hour while a solid precipitated. The solid was collected on a Buchner funnel and dried under vacuum to afford 3-(3-aminomethylphenyl)-4-methoxyaniline dihydrochloride (947 mgs, 73% yield).

Workup

  1. customThe solution was purged with hydrogen
  2. customThe reaction was purged with nitrogen
  3. customthe catalyst was removed by filtration
  4. customSolvent was removed in vacuo
  5. dissolutionthe residue was redissolved in dichloromethane (10 mL)
  6. additionhydrochloride acid was added (4.0 M solution in dioxane, 1.5 equiv., 1.57 mL)
  7. stirringThe solution was stirred for 1 hour while a solid
  8. customprecipitated
  9. customThe solid was collected on a Buchner funnel
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7736459421a347159cce0260859d86c1
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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