Hydrochloric Acid → HCID 58318861, compound

HRID 2401497Notes

Reaction equation

HRID 2401497 reaction equation
[F:1][C:2]1[CH:3]=C([CH:7]=[C:8]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:9]=1)C#N.[OH-:17].[Na+].Cl.[CH2:20]([OH:22])[CH3:21]>CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:21]([CH:7]=[C:8]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:9]=1)[C:20]([OH:17])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58318876HCID 58318876, compound

Product 1

HCID 58318861HCID 58318861, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Compound 4 (1.36 g, 6.32 mmol, 1.00 eq) was dissolved in ethanol (32 mL) and 1N NaOH (17 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (11 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 1.47 g (99%) of the title compound as a pale-yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 8.72 (s, 2H), 7.44 (ddd, J=9.2, 2.4, 1.1 Hz, 1H), 7.34-7.32 (m, 1H), 7.22 (dt, J=9.5, 2.4 Hz, 1H); [M+1]+: 235.1

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-953c0caa4d734a4caebd96ec8d2fde8b
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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