Nicotinic Acid → HCID 2836067, compound

HRID 1709946Notes

Reaction equation

HRID 1709946 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C[O-].[Na+].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:1]([O:9][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 938Nicotinic AcidHCID 660114-Nitrobenzyl bromideHCID 10942334Sodium Methoxide

Product 1

HCID 2836067HCID 2836067, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A Suspension of nicotinic acid (5.00 g, 40.6 mmol) in N,N-dimethylformaide (40 ml) was treated with sodium methoxide (2.19 g, 40.6 mmol). The resulting solution was treated with p-nitrobenzylbromide (8.77 g, 40.6 mmol) and heated at 50°, After heating 16 hrs the reaction was allowed to cool to ambient temperature and diluted with ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution and filtered. The organic fraction was separated and washed with water, brine, dried over anhydrous magnesium sulfate, filtered and evaporated under vacuum to a solid.

Workup

  1. temperatureheated at 50°
  2. temperatureAfter heating 16 hrs the reaction
  3. filtrationfiltered
  4. customThe organic fraction was separated
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum to a solid

Sources & evidence

ORD record
ord-99b9347bdaa54ff79c8209666b3e3c96
Source dataset
uspto-grants-1990_08
Patent number
US04952397

Reaction notes

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