Hydrochloric Acid → 2-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

HRID 640693Notes

Reaction equation

HRID 640693 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[NH:13][N:12]=2)=[CH:6][C:3]=1[C:4]#N.[OH-:22].[Na+].Cl.[OH2:25]>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[NH:13][N:12]=2)=[CH:6][C:3]=1[C:4]([OH:25])=[O:22]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 248117392-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzonitrile

Product 1

HCID 248117402-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

Conditions

Temperature
90 °C

Procedure

2-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzonitrile (ED) (9.60 g, 34.37 mmol) and water (40 ml) were stirred at 20° C. 2M Sodium hydroxide (36 ml, 72.00 mmol) was added, the reaction mixture warmed to 90° C. and held at this temperature overnight. The reaction mixture was cooled to room temperature and filtered. The filter pad was washed with water (10 ml) and the combined filtrate added to 2M HCl (56 ml, 112.00 mmol) at 60° C. over 40 minutes. The resulting suspension was cooled to 50° C. and filtered, washed with water (57 ml) and dried in vacuo at up to 60° C. to give the title compound as a white solid (9.72 g).

Workup

  1. customheld at this temperature overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe filter pad was washed with water (10 ml)
  5. temperatureThe resulting suspension was cooled to 50° C.
  6. filtrationfiltered
  7. washwashed with water (57 ml)
  8. customdried in vacuo at up to 60° C.

Sources & evidence

ORD record
ord-9565d265ab5548b0961bbe7fb198ce18
Source dataset
uspto-grants-2010_04
Patent number
US07692006B2

Reaction notes

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