Acetic Acid → HCID 117676244, compound

HRID 714121Notes

Reaction equation

HRID 714121 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([O:13][C:14]2[CH:15]=[CH:16][C:17]([F:24])=[C:18]([CH:23]=2)[C:19]([O:21][CH3:22])=[O:20])=[N:4][N:3]=1.C(O)(=[O:27])C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[C:5]([O:13][C:14]1[CH:15]=[CH:16][C:17]([F:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20])=[N:4][NH:3][C:2]2=[O:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 117676215HCID 117676215, compound

Product 1

HCID 117676244HCID 117676244, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-((4,8-dichlorophthalazin-1-yl)loxy)-2-fluorobenzoate (5d) (700 mg, 1.9 mmol), acetic acid (20 mL) and sodium acetate (420 mg, 3 mmol) were added into a reaction flask successively, the mixture was refluxed for one hour, and diluted with 50 mL ethyl acetate. The reaction solution was washed with 50 mL saturated sodium bicarbonate solution and saturated sodium chloride solution successively for three times, the organic layers were combined, concentrated and dried to give methyl 5-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)oxy)-2-fluorobenzoate (5e), 650 mg white solid (yield 95%). 1H NMR (600 MHZ, DMSO-d6): δ 12.12 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.95-8.00 (m, 1H), 7.83-7.87 (m, 1H), 7.74-7.77 (m, 1H), 7.61-7.64 (m, 1H), 7.42-7.47 (m, 1H), 3.86 (s, 3H); ESI-MS m/z; calculated for 348.0. found 371.6 [M+Na]+.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. washThe reaction solution was washed with 50 mL saturated sodium bicarbonate solution and saturated sodium chloride solution successively for three times
  3. concentrationconcentrated
  4. customdried

Sources & evidence

ORD record
ord-56553680422d419aa4e852800beebfc1
Source dataset
uspto-grants-2015_11
Patent number
US09187430B2

Reaction notes

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