Hydrochloric Acid → HCID 178518922, compound

HRID 1803492Notes

Reaction equation

HRID 1803492 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][N:3]=1.[OH-].[Na+].[O:27]1CCOCC1.Cl>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[CH:9][CH:10]=2)[C:5]([OH:27])=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86620966(1,4-Dichloro-phthalazin-6-yl)-(3-trifluoromethyl-benzyl)-amine

Product 1

HCID 178518922HCID 178518922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (1,4-Dichloro-phthalazin-6-yl)-(3-trifluoromethyl-benzyl)-amine (39 mg, 0.105 mmol), 2N NaOH (0.52 mL, 1.05 mmol) and dioxane (3 mL) was heated to 85° C. for 64 hours. The reaction 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. Chromatography (Hex/EtOAc) afforded 4-chloro-7-(3-trifluoromethyl-benzylamino)-phthalazin-1-ol (13 mg), 1H NMR (600 MHz, CDCl3) δ: 4.36 (d, 2H), 6.25 (t, 1H), 7.00 (dd, 1H), 7.22 (d, 1H), 7.28-7.42 (m, 3H), 7.46 (s, 1H), 7.57 (d, 1H), 11.49 (s, 1H) ppm. m/z 354.08; and 4-chloro-6-(3-trifluoromethyl-benzylamino)-phthalazin-1-ol (8 mg), 1H NMR (500 MHz, CDCl3) δ: 4.36 (d, 2H), 6.28 (t, 1H), 6.74 (d, 1H), 6.92 (dd, 1H), 7.32-7.46 (m, 3H), 7.51 (s, 1H), 7.95 (d, 1H), 11.60 (s, 1H) ppm. m/z 354.08.

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-aa5436986b9a423fb396848ebec79c8c
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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