Sodium Hydroxide → HCID 67561107, compound

HRID 2178546Notes

Reaction equation

HRID 2178546 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57690166HCID 57690166, compound

Product 1

HCID 67561107HCID 67561107, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 1-C (0.842 g, 4.12 mmol) in MeOH (10 mL) was added 3N NaOH (2.75 mL, 8.25 mmol) and the reaction mixture was refluxed for 18 h. The reaction mixture was cooled and the solvent evaporated under reduced pressure. The crude residue was dissolved in H2O and neutralized with 1N HCl to pH ˜7. The aqueous phase was evaporated to dryness under reduced pressure, and the resultant white solid was suspended in EtOH (20 mL) and stirred for 1 h. The solid was filtered and washed with EtOH. The solvent was evaporated under reduced pressure to afford compound 1-D as a white solid (0.793 g, 90%). 1H-NMR (CD3OD): δ 8.77-8.79 (t, 1H), 8.08-8.12 (m, 1H), 7.91-7.94 (m, 1H), 7.59-7.62 (m, 1H), 2.94 (s, 3H); MS: m/z 177.1 (MH+).

Workup

  1. temperaturethe reaction mixture was refluxed for 18 h
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionThe crude residue was dissolved in H2O and neutralized with 1N HCl to pH ˜7
  5. customThe aqueous phase was evaporated to dryness under reduced pressure
  6. filtrationThe solid was filtered
  7. washwashed with EtOH
  8. customThe solvent was evaporated under reduced pressure
  9. customto afford compound 1-D as a white solid (0.793 g, 90%)

Sources & evidence

ORD record
ord-0959dc144efb49b280b47bb3887b82e4
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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