Hydrochloric Acid → HCID 57436587, compound

HRID 730936Notes

Reaction equation

HRID 730936 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=2[O:20][CH3:21])[CH:8]=[CH:9][CH:10]=1)[CH3:3].Cl>CCO.O.CCO.[Fe]>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=2[O:20][CH3:21])[NH2:17])[CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57436588HCID 57436588, compound

Product 1

HCID 57436587HCID 57436587, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

2-(3-(N,N-Dimethylamino)methylphenyl)-4-nitroanisole (200 mg, 0.70 mmol) was dissolved in EtOH/H2O (5 mL:2.5 mL). concentrated HCl (40 uL) was added, followed by iron powder (314 mg). The reaction mixture was refluxed for 1 h, allowed to cool to room temperature, and diluted with EtOH (10 mL). The slurry was filtered and the filtrate evaporated. The resultant oil was taken up in 1 M NaOH (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic phases were dried (Na2SO4) and evaporated to afford 3-[3-(N,N-dimethylamino)methylphenyl]-4-methoxyaniline as a brown oil (102 mg, 0.40 mmol, 57%)

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationThe slurry was filtered
  3. customthe filtrate evaporated
  4. extractionextracted with CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-999516eaf5a5409fae2644058babfe11
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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