Hydrochloric Acid → 2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid

HRID 925063Notes

Reaction equation

HRID 925063 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=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[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=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 690434422-Fluoro-5-((3-oxo-4,5,6,7-tetrahydroisobenzofuran-1 (3h)-ylidene)methyl)benzonitrile

Product 1

HCID 250050192-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of EXAMPLE 1C (1.46 g) in water (15 mL) was added 50% sodium hydroxide. The mixture was heated at 90° C. for 1 hour. After cooling to 70° C., hydrazine monohydrate (0.54 mL) was added, and the solution was stirred at 70° C. for 17 hours. The solution was cooled to ambient temperature and brought to pH 4 with 6N hydrochloric acid. The precipitate was filtered, washed with water and dried. 1H NMR (DMSO-d6) δ1.55-1.69 (m, 4H), 2.31-2.42 (m, 4H), 3.93 (s, 2H), 7.24 (dd, J=10.8, 8.5 Hz, 1H), 7.40-7.48 (m, 1H), 7.68 (dd, J=6.9, 2.2 Hz, 1H), 12.61 (s, 1H), 13.22 (brs, 1H).

Workup

  1. temperatureAfter cooling to 70° C.
  2. temperatureThe solution was cooled to ambient temperature
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b28dc8eef0dc4a92a4aecc04a8954249
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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