Potassium Nitrate → HCID 86595480, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
200 mg of 1-Chloro-4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester, Example D-10 a, 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-787b778c5a304657846bc27fcb0db9dc
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863292B2
Reaction notes
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