Acetic Acid → HCID 178515719, compound

HRID 47064Notes

Reaction equation

HRID 47064 reaction equation
Br.CN(C)[CH:4]=[CH:5][C:6]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[CH:8][N:7]=1.CC(O)=[O:17]>>[OH:17][C:8]1[CH:9]=[CH:10][C:11]2[C:6](=[CH:5][CH:4]=[N:13][CH:12]=2)[N:7]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 54435625N,N-dimethyl-2-(3-cyano-2-pyridyl) ethenamine

Product 1

HCID 178515719HCID 178515719, compoundYield 56%

Procedure

A solution of 30% HBr in AcOH (200 mL) was added dropwise with mechanical stirring at 40° to a solution of N,N-dimethyl-2-(3-cyano-2-pyridyl)ethenamine (10.8 g, 0.062 m) in AcOH (100 mL). After the addition, the slurry was stirred at 55° for 2 hours. The mixture was then evaporated to dryness and the residue treated with ice and saturated aqueous Na2CO3. The aqueous layer was filtered and the filtrate extracted with Et2O. The aqueous layer was placed in a continuous extractor with CHCl3 to yield 7.0 g of a crude product. Sublimation of this product at 160°-180° (0.1 mm) yielded 5.1 g (56%) of hydroxy-1,6-naphthyridine. An analytical sample was prepared by crystallization from CH3OH: m.p. 243-244.5.

Workup

  1. additionAfter the addition
  2. customThe mixture was then evaporated to dryness
  3. additionthe residue treated with ice and saturated aqueous Na2CO3
  4. filtrationThe aqueous layer was filtered
  5. extractionthe filtrate extracted with Et2O
  6. customto yield 7.0 g of a crude product

Sources & evidence

ORD record
ord-b310825930f24bb88d28c48de4f8dde4
Source dataset
uspto-grants-1979_11
Patent number
US04176183

Reaction notes

Loading…