Hydrochloric Acid → HCID 89608328, compound

HRID 714118Notes

Reaction equation

HRID 714118 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([O:18]CC)=[O:17])=[N:4][NH:3]1.Cl>[OH-].[K+]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([OH:18])=[O:17])=[N:4][NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89608438HCID 89608438, compound

Product 1

HCID 89608328HCID 89608328, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Ethyl 3-((4-oxo-3,4-dihydrophthalazin-1-yl)oxy)benzoate (2d) (1 g, 3.2 mmol) obtained in the last step was dissolved in 1M potassium hydroxide solution, stirred for two hours at room temperature, and then concentrated hydrochloric acid was added dropwise to adjust pH=3, stirred for two hours at room temperature, filtrated to give a white solid intermediate 3-(4-oxo-3,4-dihydro-phthalazin-1-yl-oxyl)benzoic acid (2e), 893 mg white solid (yield 99%). 1H NMR (600 MHz, DMSO-d6): δ 11.96 (s, 1H), 8.26 (d, 1H, J=7.9 Hz), 8.12 (d, 1H, J=7.9 Hz), 8.02-7.99 (m, 1H), 7.97-7.94 (m, 1H), 7.82-7.81 (m, 2H), 7.56-7.55 (m, 2H); ESI-MS m/z: calculated for 282.1. found 281.1 [M−H]+.

Workup

  1. stirringstirred for two hours at room temperature
  2. filtrationfiltrated

Sources & evidence

ORD record
ord-69be6c853a04425b8fd35616da81f08e
Source dataset
uspto-grants-2015_11
Patent number
US09187430B2

Reaction notes

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