Ammonia → HCID 46835211, compound

HRID 2239520Notes

Reaction equation

HRID 2239520 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(O)=O)=[C:5]2O.O=S(Cl)[Cl:20].C[N:23]([CH:25]=[O:26])C.N>CC(C)=O>[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:25]([NH2:23])=[O:26])=[C:5]2[Cl:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178486927HCID 178486927, compound

Product 1

HCID 46835211HCID 46835211, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 1 L round bottom flask charged with 6-bromo-4-hydroxy-7-methoxycinnoline-3-carboxylic acid (Method 18) (14 g, 46.8 mmol) was added SOCl2 (342 ml) and DMF (1 ml). The resulting mixture was heated to reflux for 4 hours before being cooled to rt. The reaction mixture was conc. in vacuo to yield a residue which was suspended in acetone (˜400 ml). The suspension was cooled to 0° C. in an ice bath and conc. aqueous ammonia (50 ml, 1284 mmol) was added drop wise via an addition funnel and the resulting mixture was allowed to stir at 0° C. for an additional 15 minutes. A precipitate formed which was collected via vacuum filtration. The filter cake was washed with water (3×100 mL), acetone (3×50 mL), collected, and dried in vacuo to yield the title compound as an off white solid (14.00 g, 94%) which was used without further purification. 1H NMR: 8.55 (s, 1H), 8.40 (s, 1H), 8.05 (m, 2H), 4.10 (s, 3H); m/z: 317.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. customto yield a residue which
  4. temperatureThe suspension was cooled to 0° C. in an ice bath
  5. customA precipitate formed which
  6. filtrationwas collected via vacuum filtration
  7. washThe filter cake was washed with water (3×100 mL), acetone (3×50 mL)
  8. customcollected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d12ecb43a15f4323a3815a8440a40cbc
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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