Hydrochloric Acid → HCID 58318871, compound

HRID 2401505Notes

Reaction equation

HRID 2401505 reaction equation
[F:1][C:2]1[CH:3]=C([CH:7]=[C:8]([N:10]([CH3:17])[C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:9]=1)C#N.[OH-:18].[Na+].Cl.[CH2:21]([OH:23])[CH3:22]>CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:22]([CH:7]=[C:8]([N:10]([CH3:17])[C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:9]=1)[C:21]([OH:18])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58318783HCID 58318783, compound

Product 1

HCID 58318871HCID 58318871, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Compound 12 (0.860 g, 3.77 mmol, 1.00 eq) was dissolved in ethanol (16 mL) and 1N NaOH (8 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (8 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 0.852 g (91%) of the title compound as a pale-yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.85 (s, 1H), 8.65 (s, 2H), 7.35-7.32 (m, 1H), 7.26-7.18 (m, 2H), 3.36 (s, 3H); [M+1]+: 248.2.

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-09912caeaddc4b69bce1fd786a483b5d
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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