Hydrochloric Acid → 2-Isoquinolin-3-yl-3-methyl-chromen-4-one oxime

HRID 1853297Notes

Reaction equation

HRID 1853297 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[O:12][C:13]3[C:18]([C:19](=O)[C:20]=2[CH3:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1.Cl.[NH2:24][OH:25].Cl>N1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[O:12][C:13]3[C:18]([C:19](=[N:24][OH:25])[C:20]=2[CH3:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 671958072-Isoquinolin-3-yl-3-methyl-chromen-4-one

Product 1

HCID 1363522382-Isoquinolin-3-yl-3-methyl-chromen-4-one oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 2-Isoquinolin-3-yl-3-methyl-chromen-4-one (example 71A) (200 mg, 0.69 mmol) in anhydrous pyridine (5 ml) was added hydroxylamine hydrochloride (96 mg, 1.39 mmol). The mixture was heated to 130° C. under microwave irradiation for 30 min. The reaction mixture was poured into a 1N aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with a 1N aqueous solution of hydrochloric acid, brine and dried over sodium sulfate and concentrated. The title compound was isolated as a white solid after Preparative HPLC purification (gradient 45-30% Water/Methanol+0.05% trifluoroacetic acid) (9 mg, 4%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with a 1N aqueous solution of hydrochloric acid, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c10bebea1b74c1dbef43f2771aed1ed
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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