Ethanol → HCID 57791854, compound

HRID 1091783Notes

Reaction equation

HRID 1091783 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:21])=C([CH:20]=1)C#N)=[N:9][NH:8][C:7]2=[O:22].[OH-:23].[K+].[CH2:25]([OH:27])[CH3:26]>O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:21])=[C:26]([CH:20]=1)[C:25]([OH:23])=[O:27])=[N:9][NH:8][C:7]2=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 577918005-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile

Product 1

HCID 57791854HCID 57791854, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile (102) (6.1 g, 19.44 mmol) and potassium hydroxide (10.91 g, 194.44 mmol) were added to ethanol (30 mL) and water (70 mL) and heated at 100° C. for 5 hours. The ethanol was evaporated off and the aqueous was extracted with ethyl acetate (1×75 mL). The aqueous was then acidified to pH1 with conc HCl to afford a solid, this was filtered, washed with water and dried to afford the desired compound as a beige solid (5.73 g, 89%); 1H NMR (400.132 MHz, DMSO) δ 4.63 (2H, s), 7.21 (1H, dd), 7.44-7.40 (1H, m), 7.64 (1H, dd), 7.82 (1H, t), 7.98 (1H, dd), 8.34 (1H, dd), 12.87 (1H, s), 13.12 (1H, s); m/z (LC-MS, ESI+), RT=0.87 (M+H 333).

Workup

  1. customThe ethanol was evaporated off
  2. extractionthe aqueous was extracted with ethyl acetate (1×75 mL)
  3. customto afford a solid
  4. filtrationthis was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-278bd6097e594db2a89168a02f833ac0
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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