Hydrochloric Acid → HCID 178522037, compound

HRID 1667413Notes

Reaction equation

HRID 1667413 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([I:22])=[N:17][N:16]=[C:15]3I)=[O:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[O:28]1CCOCC1.Cl>O>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([I:22])=[N:17][N:16]=[C:15]3[OH:28])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86620962HCID 86620962, compound

Product 1

HCID 178522037HCID 178522037, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1,4-di-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (0.15 g, 0.264 mmol), 2N NaOH (1.32 mL, 2.64 mmol) and dioxane (3 mL) was stirred at 50° C. for 16 h. The reaction mixture was diluted with water, acidified with conc. HCl to ˜pH 4 and extracted with EtOAc (×3). The combined organic phase was washed with brine, dried (Na2SO4) and concentrated to afford 1-iodo-4-hydroxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (27 mg), 1H NMR (600 MHz, CDCl3) δ: 7.20 (d, 1H), 7.31 (t, 1H), 7.72 (d, 1H), 7.96 (d, 1H), 8.00 (s, 1H), 8.33 (dd, 1H), 8.86 (s, 1H), 10.40 (s, 1H), 12.39 (s, 1H) ppm. m/z 460.07; and 4-iodo-1-hydroxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (27 mg), 1H NMR (500 MHz, CDCl3) δ: 7.27 (d, 1H), 7.38 (t, 1H), 8.00 (m, 2H), 8.24 (m, 2H), 8.30 (d, 1H), 10.32 (s, 1H), 12.34 (s, 1H) ppm. m/z 460.07.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74aa3e7eddba47d7b251f2af95b5be95
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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