Hydroxyamine hydrochloride → 5-(Isoquinolin-6-yl)isoxazol-3-amine

HRID 598842Notes

Reaction equation

HRID 598842 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[C:12][C:13]#[N:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl.[NH2:16][OH:17]>CCO.[OH-].[Na+].CCOC(C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:17][N:16]=[C:13]([NH2:14])[CH:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 579506673-(Isoquinolin-6-yl)propiolonitrile

Product 1

HCID 579507145-(Isoquinolin-6-yl)isoxazol-3-amineYield 98%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-(Isoquinolin-6-yl)propiolonitrile (0.060 g, 0.34 mmol) was suspended in 3.0 mL of EtOH. Hydroxylamine hydrochloride (0.070 g, 1.0 mmol) was added to the mixture in 1.5 mL of 10% aq. NaOH. The solution turned a clear, light yellow color immediately. After 3 hours, the reaction mixture was diluted with 20 mL of EtOAc and transferred to a separatory funnel. The mixture was washed with 3 mL of water and 5 mL of brine. The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure, affording 5-(isoquinolin-6-yl)isoxazol-3-amine (0.070 g, 98% yield) as a yellow solid. MS m/z: 212 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 9.36 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 8.40 (s, 1H), 8.23 (d, J=8.6 Hz, 1H), 8.05 (d, J=8.4 Hz, 1H), 7.93 (d, J=5.9 Hz, 1H), 6.57 (s, 1H).

Workup

  1. customtransferred to a separatory funnel
  2. washThe mixture was washed with 3 mL of water and 5 mL of brine
  3. dry with materialThe organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-894e8b6fc8064c7aa7fbe87c37aedf9f
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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