Potassium Nitrate → HCID 86595480, compound

HRID 1406242Notes

Reaction equation

[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:26])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[N+:27]([O-])([O-:29])=[O:28].[K+]>S(=O)(=O)(O)O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:26])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -20 °C

Procedure

200 mg of 1-Chloro-4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester, Example D-10a, was dissolved in 3 ml of concentrated sulfuric acid. The reaction mixture was cooled to −20° C. and 60 mg of potassium nitrate was added slowly to the stirring solution. The reaction was kept between −10 to −20° C. while stirring for 15 min, and poured into ice-water. The aqueous mixture was extracted twice with ethyl acetate. The organic fractions were washed successively with saturated bicarbonate and brine solutions, dried over anhydrous magnesium sulfate, and concentrated to a residue under reduced pressure. The resultant solid was triturated with ethyl acetate followed by methanol to produce 103 mg of white solid; MS (+): m/z 417.07 (M+1).

Workup

customwas kept between −10 to −20° C.
extractionThe aqueous mixture was extracted twice with ethyl acetate
washThe organic fractions were washed successively with saturated bicarbonate and brine solutions
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated to a residue under reduced pressure
customThe resultant solid was triturated with ethyl acetate

Sources & evidence

ORD record: ord-092b2a2cc67a41489f0cbaa5d3e10f4e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916585B2

Reaction notes

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