Triethylamine → HCID 67083817, compound

HRID 2239521Notes

Reaction equation

HRID 2239521 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[N:7][C:6]([C:14]([NH2:16])=O)=[C:5]2[Cl:17].O=P(Cl)(Cl)Cl.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[N:7][C:6]([C:14]#[N:16])=[C:5]2[Cl:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 46835211HCID 46835211, compound

Product 1

HCID 67083817HCID 67083817, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-bromo-4-chloro-7-methoxycinnoline-3-carboxamide (Method 21) (12 g, 37.9 mmol) in DCM (400 ml) was added POCl3 (200 ml). Triethylamine (15 ml) was then added carefully to the mixture which was stirred at reflux for 7 h. The reaction was then allowed to cool to rt and conc. in vacuo. The crude residue was then carefully treated with sat'd aqueous NaHCO3 at 0° C. A precipitate formed which was collected via vacuum filtration. The filter cake washed with water (˜100 mL), collected, and dried in vacuo to provide the title compound as a grey solid (9.80 g, 87%) which was used without further purification. 1H NMR: 8.71 (s, 1H), 8.29 (s, 1H), 4.30 (s, 3H); m/z: 299.

Workup

  1. temperatureat reflux for 7 h
  2. customA precipitate formed which
  3. filtrationwas collected via vacuum filtration
  4. washThe filter cake washed with water (˜100 mL)
  5. customcollected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d2dd73bbe5544d85a36461adfd111332
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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