Furfural → HCID 20257403, compound

HRID 1583936Notes

Reaction equation

HRID 1583936 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8](=O)[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.[BH4-].[Na+]>C1C=CC=CC=1>[CH2:8]([C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 104392-AminopyridineHCID 4311764Sodium borohydride

Product 1

HCID 20257403HCID 20257403, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 20 g (0.213 mol) of 2-aminopyridine and 22.5 g (0.234 mol) of furfural in 400 ml of benzene was refluxed for 2 hours. The benzene was then evaporated off and the residue was taken up with 500 ml of methanol. The mixture was stirred in an ice bath whereupon 8.9 g (0.234 mol) of NaBH4 were added in small portions. The mixture was then stirred at ambient temperature for 5 hours. After the methanol had been evaporated off, the residue was extracted with ether to give 24.1 g of furfuryl aminopyridine having a boiling point of b.p. 0.1=98° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe benzene was then evaporated off
  3. additionwere added in small portions
  4. customAfter the methanol had been evaporated off
  5. extractionthe residue was extracted with ether

Sources & evidence

ORD record
ord-b4ebbc2a2f224aa495fd3ef3e069f28d
Source dataset
uspto-grants-1985_11
Patent number
US04555514

Reaction notes

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