Acetic Anhydride → HCID 21405359, compound

HRID 972759Notes

Reaction equation

HRID 972759 reaction equation
[Br:1][CH:2]([Br:15])[C:3]1[N:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6].[C:16](OC(=O)C)(=[O:18])[CH3:17].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[C:16]([NH:7][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[N:11][C:3]=1[CH:2]([Br:1])[Br:15])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 214053732-(Dibromomethyl)-5-nitropyridine-3-carboxamide

Product 1

HCID 21405359HCID 21405359, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 0.48 g of 2-dibromomethyl-5-nitronicotinamide and acetic anhydride was stirred with 3 drops of conc. sulfuric acid at room temperature for 1 hour. The reaction mixture was poured into ice-water, made alkaline with 5% sodium bicarbonate and extracted with ethyl acetate. The extract was dried and the solvent was distilled off to give 0.35 g of crystalline substance, which was then recrystallized from ethyl acetate-n-hexane to give the desired product as yellow needles. mp 168° C. (with decomp.)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. distillationthe solvent was distilled off
  4. customto give 0.35 g of crystalline substance, which
  5. customwas then recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-9a7dd89c78c74c27ae18c0ba228f56fb
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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