Ethanol → HCID 57791829, compound

HRID 1091777Notes

Reaction equation

HRID 1091777 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][N:8]=[C:9]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:21])=C([CH:20]=2)C#N)=[CH:4][CH:3]=1.[OH-:23].[K+].[CH2:25]([OH:27])[CH3:26]>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][N:8]=[C:9]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:21])=[C:26]([CH:20]=2)[C:25]([OH:23])=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 57791832HCID 57791832, compound

Product 1

HCID 57791829HCID 57791829, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-((7-bromo-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile (96) (2.4 g, 6.70 mmol) and potassium hydroxide (3.76 g, 67.01 mmol) were added to ethanol (20 mL) and water (80 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, which was filtered, washed with water and dried to the desired material as a beige solid. (2.000 g, 79% yield); 1H NMR (400.132 MHz, DMSO) δ 4.37 (2H, s), 7.26 (1H, t), 7.61-7.57 (1H, m), 7.83-7.82 (1H, m), 8.01 (1H, d), 8.18 (1H, d), 8.22 (1H, s), 12.67 (1H, s), 13.19 (1H, s); m/z (LC-MS, ESI+), RT=0.88 (M+H 376).

Workup

  1. customThe ethanol was evaporated off
  2. extractionthe aqueous was extracted with ethyl acetate (1×75 mL)
  3. customto afford a solid, which
  4. filtrationwas filtered
  5. washwashed with water
  6. dry with materialdried to the desired material as a beige solid
  7. customm/z (LC-MS, ESI+), RT=0.88 (M+H 376)

Sources & evidence

ORD record
ord-98bbb96e00224a22bcb47951b74943eb
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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