Ammonium Chloride → 3-[(Dimethylamino)methyl]-4-fluoroaniline

HRID 1257266Notes

Reaction equation

HRID 1257266 reaction equation
[NH4+].[Cl-].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[CH2:13][N:14]([CH3:16])[CH3:15]>CCO.[Fe]>[CH3:16][N:14]([CH2:13][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:4]=1[F:3])[NH2:10])[CH3:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58998500HCID 58998500, compound

Product 1

HCID 450889853-[(Dimethylamino)methyl]-4-fluoroanilineYield 72.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A mix of satd. NH4Cl (5.19 mL) in EtOH (8 mL) was treated with 1-(2-fluoro-5-nitrophenyl)-N,N-dimethylmethanamine (494 mg, 2.49 mmol), followed by iron powder (1.39 g, 24.93 mmol) and heated at 55° C. overnight. The mixture was cooled to RT, the solids removed via filtration through diatomaceous earth and washed with 10% MeOH/DCM. The filtrate was concentrated to dryness, the residue treated with DCM, sonicated and the resulting solid collected via filtration, washed with THF and dried to afford 3-((dimethylamino)methyl)-4-fluoroaniline (305 mg, 72% yield). MS (ESI) m/z: 169.1 [M+H]+.

Workup

  1. additionA mix of satd
  2. temperatureThe mixture was cooled to RT
  3. customthe solids removed via filtration through diatomaceous earth
  4. washwashed with 10% MeOH/DCM
  5. concentrationThe filtrate was concentrated to dryness
  6. additionthe residue treated with DCM
  7. customsonicated
  8. filtrationthe resulting solid collected via filtration
  9. washwashed with THF
  10. customdried

Sources & evidence

ORD record
ord-cdca075e005d4d23a9902568656447dd
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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