Hydrogen Bromide → HCID 178522039, compound

HRID 1667417Notes

Reaction equation

HRID 1667417 reaction equation
[F:1][C:2]([F:31])([F:30])[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]([O:22]C)=[N:17][N:16]=[C:15]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.Br>O1CCOCC1>[F:31][C:2]([F:1])([F:30])[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]([OH:22])=[N:17][N:16]=[C:15]3[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67417444HCID 67417444, compound

Product 1

HCID 178522039HCID 178522039, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-methoxy-4-phenyl-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (80 mg, 0.189 mmol), dioxane (2 mL) and 48% HBr (4 mL) was stirred at 40° C. for 48 hours. Concentration followed by chromatography (Hex/EtOAc) afforded 1-hydroxy-4-phenyl-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (12 mg) as a white solid, 1H (500 MHz, CDCl3, 55° C.) δ: 7.47 (d, 1H), 7.52 (t, 1H), 7.56-7.65 (m, 5H), 7.84 (d, 1H), 7.90-7.96 (m, 2H), 8.21 (d, 1H), 8.29 (s, 1H), 8.65 (d, 1H), 10.40 (s, 1H) ppm. m/z 410.00.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-174a25286c134d59b8c95edfc735b07e
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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