Nitric Acid → N-(2-hydroxyethyl)nicotinamide

HRID 2050174Notes

Reaction equation

HRID 2050174 reaction equation
[N+]([O-])(O)=O.[OH:5][CH2:6][CH2:7][NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.[N+]([O-])(O)=O>C(OCC)C>[OH:5][CH2:6][CH2:7][NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23622153HCID 23622153, compound

Product 1

HCID 72663N-(2-hydroxyethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-(2-hydroxyethyl) nicotinamide nitrate (1.145 g) was gradually added to 3 ml of fuming nitric acid which had been cooled to a temperature of from -10° to -5° C. while stirring. After stirring for an additional one hour at 0°-5° C., diethyl ether was added to the solution to precipitate 1.15 g of nitric ester of N-(2-hydroxyethyl) nicotinamide nitric acid ester as colorless crystals. The crystals were dissolved in a sodium carbonate aqueous solution and ethyl acetate was added to the solution. The ethyl acetate layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was crystallized from diethyl ether to give nitric ester of N-(2-hydroxyethyl) nicotinamide. Recrystallization from diethyl ether afforded colorless crystals having a melting point of 90°-92° C.

Workup

  1. temperaturehad been cooled to a temperature of from -10° to -5° C.
  2. stirringAfter stirring for an additional one hour at 0°-5° C.
  3. customto precipitate 1.15 g of nitric ester of N-(2-hydroxyethyl) nicotinamide nitric acid ester as colorless crystals
  4. dissolutionThe crystals were dissolved in a sodium carbonate aqueous solution and ethyl acetate
  5. additionwas added to the solution
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-0291e0377d404e45ab4b8c1ebfac3967
Source dataset
uspto-grants-1980_04
Patent number
US04200640

Reaction notes

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