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

HRID 1466738Notes

Reaction equation

HRID 1466738 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[O:12]2)=[CH:6][C:3]=1[C:4]#N.[OH-:21].[Na+].[OH2:23].[NH2:24][NH2:25].Cl>O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:12])[NH:25][N:24]=2)=[CH:6][C:3]=1[C:4]([OH:23])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 671224512-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

Product 1

HCID 248117402-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the mixture of 2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile (1.2 g, 4.5 mmol) in water (6.5 ml) was added aqueous sodium hydroxide (0.84 g in 1.6 ml of water) drop-wise, then heated at 90 for 1 h. After cooled to 70, hydrazine hydrate (6.4 ml) was added and the reaction mixture was heated at 70 for overnight. Then the reaction mixture was cooled to room temperature, and adjusted to PH 3-4 by adding aqueous HCl (2N). The precipitated solid was collected by filtration, washed with water, and dried in vacuo to afford the target compound (0.9 g, 70%) as a pink solid, used in next step without further purification.

Workup

  1. temperatureheated at 90 for 1 h
  2. additionwas added
  3. temperaturethe reaction mixture was heated at 70 for overnight
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1a8155d0834b4b71b4dc3cbb37259310
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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