Acetic Anhydride → 6-Acetamido-8-bromo-1,7-naphthyridine

HRID 2308598Notes

Reaction equation

HRID 2308598 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 138267326-Acetamido-8-bromo-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Suspended in 32 ml of pyridine was 4.84 g of 6-amino-8-bromo-1,7-naphthyridine, followed by an addition of 66 ml of acetic anhydride. The resultant mixture was stirred at room temperature for 4 hours. After the reaction, the reaction mixture was poured in 500 ml of ice water and crystals, which precipitated out, were collected by filtration and then washed thoroughly with water. They were recrystallized from methanol to obtain 5.37 g of 6-acetamido-8-bromo-1,7-naphthyridine as colorless needle-like crystals (yield: 93.4%).

Workup

  1. customAfter the reaction
  2. customcrystals, which precipitated out
  3. filtrationwere collected by filtration
  4. washwashed thoroughly with water
  5. customThey were recrystallized from methanol

Sources & evidence

ORD record
ord-fe7adc4bc403478bb208bcdc40a80602
Source dataset
uspto-grants-1987_09
Patent number
US04690924

Reaction notes

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