4-Fluorobenzyl chloride → HCID 19907879, compound

HRID 845773Notes

Reaction equation

HRID 845773 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].Cl[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.[OH-].[NH4+]>ClC(Cl)Cl>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:4]2[CH:5]=[CH:6][N:1]=[C:2]([NH2:8])[C:3]=2[NH2:7])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 99562,3-DiaminopyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 19907879HCID 19907879, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3 parts of 2,3-pyridinediamine and 4 parts of 1-(chloromethyl)-4-fluorobenzene was stirred overnight at 120° C. Trichloromethane and a dilute ammonium hydroxide solution were added and the product was extracted. The organic phase was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The second fraction was collected and the eluent was evaporated, yielding 1.8 parts of N3 -[(4-fluorophenyl)methyl]-2,3-pyridinediamine as a residue (intermediate 18)

Workup

  1. extractionthe product was extracted
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  8. customThe second fraction was collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0418009e36604863b9abe458c238deac
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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