Ammonium Hydroxide → 5-Bromonicotinamide

HRID 1586619Notes

Reaction equation

HRID 1586619 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[NH4+:11].[OH-]>COCCOC>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:11])=[O:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 18085-Bromonicotinamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

All of the 5-bromonicotinoyl chloride prepared above was dissolved in 100 ml hot 1,2-dimethyoxyethane and added slowly during about 15 min to 500 ml cold, concentrated NH4OH in a 1 l round-bottom flask. The mixture was then stirred 1.5 hr at -10° C. to about 5° C. followed by filtration to collect white crystalline plates of 5-bromonicotinamide which were dried at 56° C. for 1.0 min to afford 17.79 g (89.2% yield) mp 222°-223° C. (lit. 224°-225° C., Czuba, W., Rec Trav Chim (1963) 82: 988-996; lit 141°-142° C., Morisawa, Y., J Med Chem (1977) 20: 129).

Workup

  1. additionadded slowly during about 15 min to 500 ml cold
  2. filtrationfollowed by filtration
  3. customto collect white crystalline plates of 5-bromonicotinamide which
  4. customwere dried at 56° C. for 1.0 min
  5. customto afford 17.79 g (89.2% yield) mp 222°-223° C. (lit. 224°-225° C., Czuba, W., Rec Trav Chim (1963) 82: 988-996; lit 141°-142° C., Morisawa, Y., J Med Chem (1977) 20: 129)

Sources & evidence

ORD record
ord-5d45c423a8ba40dfa1e8268ae6ed79cb
Source dataset
uspto-grants-1993_06
Patent number
US05215738

Reaction notes

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