Hydrochloric Acid → HCID 43144877, compound

HRID 1908970Notes

Reaction equation

HRID 1908970 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]#N)[CH:9]=2)[CH:2]=1.[OH-:16].[Na+].Cl.C[OH:20].C(Cl)Cl>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([OH:20])=[O:16])[CH:9]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 55209004HCID 55209004, compound

Product 1

HCID 43144877HCID 43144877, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (1.5 g, 7.6 mmol, 1.0 eq) was dissolved in ethanol (30 mL) and 1N NaOH (15 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (15 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 the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J=2.7 Hz, 1H), 8.39-8.36 (m, 2H), 8.06 (ddd, J=8.7, 2.7, 1.1 Hz, 1H), 7.88 (dd, J=8.7, 5.4 Hz, 1H), 7.40 (d, J=2.2 Hz, 1H), 7.12 (dd, J=5.7, 2.4 Hz, 1H); ES-MS [M+1]+: 217.1.

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-b9e701fab6cc4adea3c1ec081d1fbcdc
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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