hydroxylamine-O-sulfonic acid → 7-Bromo-[1,2,4]triazolo[1,5-a]quinoline

HRID 2075708Notes

Reaction equation

HRID 2075708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[CH:6]=[CH:5]2.CO[CH:15]([N:18](C)C)OC.NOS(O)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[N:18]=[CH:15][N:12]=[C:7]1[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 76284hydroxylamine-O-sulfonic acidHCID 78373Dimethylformamide dimethyl acetalHCID 111836666-Bromoquinolin-2-amine

Product 1

HCID 582577957-Bromo-[1,2,4]triazolo[1,5-a]quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

8a (497 mg, 2.46 mmol) and dimethoxymethyldimethylamine (1 mL) were combined in DMF (5 mL) and heated to 130° C. for 1 hour. The reaction was concentrated and redissolved in MeOH (5 mL) and pyridine (400 mg). Hydroxylamine-O-sulfonic acid (282 mg, 2.49 mmol) was added, and the mixture was stirred at room temperature for 3 days. The solution was concentrated and poured into water, and the resulting solid was filtered and dried to give the desired product, 8b.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in MeOH (5 mL)
  3. concentrationThe solution was concentrated
  4. additionpoured into water
  5. filtrationthe resulting solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-71450a1d309f4490b06142bc19084c68
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

Loading…