Acetic Acid → 2,3-Dihydrocinnolin-4(1H)-one--hydrogen chloride (1/1)

HRID 902046Notes

Reaction equation

HRID 902046 reaction equation
[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.C(O)(=O)C>C(O)C.[Zn]>[ClH:1].[NH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178479639HCID 178479639, compound

Product 1

HCID 145320182,3-Dihydrocinnolin-4(1H)-one--hydrogen chloride (1/1)Yield 60%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
-15 °C

Procedure

69.41 g of the product obtained in stage A are dissolved in 2.5 l of ethanol. 62.79 g of zinc powder are subsequently added, followed, slowly, by a mixture of 300 ml of ethanol and 150 ml of acetic acid at ambient temperature. The mixture is heated at reflux for 30 min. The reaction medium is subsequently separated by settling, and the zinc residue is washed several times with ethanol. After being allowed to cool for 20 minutes in an ice/methanol mixture (−15° C.), a solution of hydrogen chloride gas in ethyl acetate is then added (350 ml; 4M). The precipitate formed is filtered off, washed with ether and then with pentane, and finally dried (under reduced pressure). 42.12 grams (60%) of the expected product are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 min
  3. customThe reaction medium is subsequently separated
  4. washthe zinc residue is washed several times with ethanol
  5. additiona solution of hydrogen chloride gas in ethyl acetate is then added (350 ml; 4M)
  6. customThe precipitate formed
  7. filtrationis filtered off
  8. washwashed with ether
  9. dry with materialwith pentane, and finally dried (under reduced pressure)

Sources & evidence

ORD record
ord-32ea3e108fa44b7084578ed26a79caee
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

Loading…