Formamide → N-(1-pyridin-4-ylethyl)formamide

HRID 1831806Notes

Reaction equation

HRID 1831806 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH3:8])=[CH:3][CH:2]=1.[CH:10]([NH2:12])=[O:11].[OH-].[Na+]>C(O)=O.O>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH:12][CH:10]=[O:11])[CH3:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 713FormamideHCID 142824-AcetylpyridineHCID 14798Sodium Hydroxide

Product 1

HCID 2771720N-(1-pyridin-4-ylethyl)formamide

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 962WaterSolvent

Procedure

1-Pyridin-4-yl-ethanone (24.2 g, 199.77 mmol) and 10 ml of formic acid were heated to 180° C. and formamide (126 g, 2.797 mol) in 10 ml of formic acid was added within 30 min. The mixture was stirred for 90 min., cooled and poured in 100 ml of water. After addition of conc. sodium hydroxide solution until pH13 the product was extracted with diethyl-ether. The organic layer was dried with MgSO4 and evaporated. Purification by distillation (165° C./4 mbar) yields pure product.

Workup

  1. temperaturecooled
  2. extractionwas extracted with diethyl-ether
  3. dry with materialThe organic layer was dried with MgSO4
  4. customevaporated
  5. customPurification
  6. distillationby distillation (165° C./4 mbar)
  7. customyields pure product

Sources & evidence

ORD record
ord-51a7bbae96154048b61fe7ecbbdc2a52
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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