Hydrogen Bromide → HCID 178494317, compound

HRID 1667421Notes

Reaction equation

HRID 1667421 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][N:6]=[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][CH3:23])=[N:17][N:16]=[C:15]3[O:24]C)=[O:11])[CH:4]=1.Br.[OH-].[Na+]>O1CCOCC1>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:8]=[CH:7][N:6]=[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][CH3:23])=[N:17][N:16]=[C:15]3[OH:24])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67418127HCID 67418127, compound

Product 1

HCID 178494317HCID 178494317, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,4-dimethoxy-phthalazine-6-carboxylic acid (4-trifluoromethyl-pyridin-2-yl)-amide (0.24 g, 0.634 mmol), dioxane (3 mL) and 48% HBr (0.1 mL) was stirred at room temperature for 18 hours. The reaction was poured onto water, neutralized with 2N NaOH and extracted with EtOAc. The combined organic layers were washed with water, brine and dried (Na2SO4). Chromatography (Hex/EtOAc) afforded 4-hydroxy-1-methoxy-phthalazine-6-carboxylic acid (4-trifluoromethyl-pyridin-2-yl)-amide (5 mg), m/z (M+1) 379.11; and 1-hydroxy-4-methoxy-phthalazine-6-carboxylic acid (4-trifluoromethyl-pyridin-2-yl)-amide (16 mg), 1H NMR (600 MHz, CDCl3) δ: 3.94 (s, 3H), 7.26 (d, 1H), 8.29 (dd, 1H), 8.41 (d, 1H), 8.46 (d, 1H), 8.50 (s, 1H), 8.62 (s, 1H), 9.75 (s, 1H), 10.53 (s, 1H) ppm. m/z 364.95.

Workup

  1. additionThe reaction was poured onto water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-981fc09803cf473987172bceec7a3126
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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