Hydrochloric Acid → 2-[2-[5-(4-Nitrophenyl)furfurylamino]ethyl]pyridine Dihydrochloride

HRID 1904056

Reaction equation

HRID 1904056 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([CH:15]=O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.[BH4-].[Na+].[ClH:28]>CO>[ClH:28].[ClH:28].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([CH2:15][NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 759192-PyridineethanamineHCID 815675-(4-Nitrophenyl)-2-furaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 132776072-[2-[5-(4-Nitrophenyl)furfurylamino]ethyl]pyridine DihydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A mixture of 54 g (0.25 mole) of 5-(4-nitrophenyl)-2-furaldehyde and 30.5 g (0.25 mole) of 2-(2-aminoethyl)pyridine in 300 ml of methanol was heated under reflux for 21/2 hours. The resulting solution was cooled to 25°, and 9.5 g (0.25 mole) of sodium borohydride was added in portions over 1 hour at 25°-30°. The solution was heated under reflux for 15 min, and the solvent was removed on a rotary evaporator. The residual solid was partitioned between water and chloroform. The chloroform layer (400 ml) was separated, dried over MgSO4, and concentrated on a rotary evaporator to give 81 g of a reddish brown, oily residue which solidified on standing. The residual solid was dissolved in 400 ml of absolute methanol and treated with 200 ml of absolute methanol saturated with hydrogen chloride with cooling in ice. The yellow solid which was deposited was collected by filtration using a rubber dam and dried in a vacuum oven at oil pump pressure at 100° C. for 8 hr to give 86 g (87%) of product. Two additional recrystallizations from absolute methanol gave an analytical sample, m.p. 173°-177°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21/2 hours
  3. temperatureThe resulting solution was cooled to 25°
  4. temperatureThe solution was heated
  5. temperatureunder reflux for 15 min
  6. customthe solvent was removed on a rotary evaporator
  7. customThe residual solid was partitioned between water and chloroform
  8. customThe chloroform layer (400 ml) was separated
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated on a rotary evaporator
  11. customto give 81 g of a reddish brown, oily residue which
  12. temperaturewith cooling in ice
  13. filtrationThe yellow solid which was deposited was collected by filtration
  14. customdried in a vacuum oven at oil pump pressure at 100° C. for 8 hr

Sources & evidence

ORD record
ord-4f9cae1a96b045d9b084da89dcf8d88e
Source dataset
uspto-grants-1984_03
Patent number
US04439608

Linked notes

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