Hydrochloric Acid → HCID 86620968, compound

HRID 1803501Notes

Reaction equation

HRID 1803501 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.[CH3:26][O-:27].[Na+].Cl>CN(C=O)C>[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[O:27][CH3:26])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86620962HCID 86620962, compound

Product 1

HCID 86620968HCID 86620968, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,4-di-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (0.59 g, 1.037 mmol), sodium methoxide (0.11 g, 2.036 mmol) in DMF (8 mL) was stirred at room temperature for 18 hours. The reaction was poured onto water, neutralized with 2N HCl. The product was extracted with EtOAc (×3), the combined organic extracts washed with water (×3), brine and dried (Na2SO4). Chromatography (Hex/EtOAc) afforded 1-iodo-4-methoxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (134 mg), m/z 473.91; and 4-iodo-1-methoxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (132 mg), m/z 473.91.

Workup

  1. additionThe reaction was poured onto water
  2. extractionThe product was extracted with EtOAc (×3)
  3. washthe combined organic extracts washed with water (×3), brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-22e1c24c0c85442c88279d8866552a6a
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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