Hydrochloric Acid → HCID 58318808, compound

HRID 2401509Notes

Reaction equation

HRID 2401509 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1)[C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C#N.[OH-:17].[Na+].Cl.[CH2:20]([OH:22])[CH3:21]>CO.C(Cl)Cl>[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1)[C:3]1[CH:4]=[C:21]([CH:8]=[CH:9][CH:10]=1)[C:20]([OH:17])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58318777HCID 58318777, compound

Product 1

HCID 58318808HCID 58318808, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Compound 16 (0.735 g, 3.50 mmol, 1.00 eq) was dissolved in ethanol (15 mL) and 1N NaOH (7.5 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (7.5 mL) and the reaction was concentrated in vacuo. The crude reaction was dissolved in 10% MeOH/CH2Cl2 and the undissolved salt was filtered off and the solvents were removed in vacuo to afford 0.710 g (89%) of the title compound as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 8.45 (s, 2H), 7.69-7.64 (m, 2H), 7.48 (t, J=8.3 Hz, 1H), 7.43-7.39 (m, 1H), 3.34 (s, 3H); [M+1]+: 230.2.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureafter cooling the reaction
  3. concentrationthe reaction was concentrated in vacuo
  4. customThe crude reaction
  5. filtrationthe undissolved salt was filtered off
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-3a078a3925fb47e886f29e006692221c
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

Loading…