Hydrochloric Acid → HCID 24947220, compound

HRID 1803591Notes

Reaction equation

HRID 1803591 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([Cl:23])=[N:18][N:17]=[C:16]3Cl)=[O:12])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].[O:29]1CCOCC1.Cl>O>[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:19]([Cl:23])=[N:18][NH:17][C:16]3=[O:29])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86620976HCID 86620976, compound

Product 1

HCID 24947220HCID 24947220, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (350 mg, 0.87 mmol), 2N NaOH (4.4 mL, 8.70 mmol) and dioxane (4 mL) was heated to 50° C. for 3 h. The reaction was diluted with water, acidified with conc. HCl to ˜pH 6. The reaction mixture was concentrated to low volume and filtered through celite. Chromatography (Hex/EtOAc) afforded 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (14 mg) as a white solid, 1H NMR (400 MHz, d6-DMSO) δ: 7.14 (m, 1H), 7.52 (t, 1H), 7.82 (d, 1H), 7.95 (s, 1H), 8.14 (d, 1H), 8.53 (dd, 1H), 8.89 (s, 1H), 10.88 (s, 1H), 13.04 (s, 1H) ppm; m/z (M+1) 384.05; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (20 mg) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 7.06 (d, 1H), 7.44 (t, 1H), 7.70 (d, 1H), 7.85 (s, 1H), 8.34 (m, 2H), 8.39 (s, 1H), 10.87 (s, 1H), 12.92 (s, 1H) ppm; m/z (M+1) 384.05.

Workup

  1. concentrationThe reaction mixture was concentrated to low volume
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-dd354a1b674b4c3294c28d699a0393fa
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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