Sodium Carbonate → HCID 178430466, compound

Temperature

85 °C

Prepared using General Procedure 1. To 3-methylisonicotinonitrile (0.500 g, 4.2 mmol) in EtOH (7 mL) was added hydroxylamine hydrochloride (0.588 g, 8.5 mmol) and Na2CO3 (1.34 g, 12.7 mmol) and the reaction mixture was heated at 85° C. for 4 h. Once cooled to room temperature, the reaction mixture was filtered using EtOH to rinse the filter cake. The filtrate was concentrated under reduced pressure. The resulting pale yellow solid was triturated with ice water (50 mL), filtered, and the solid was washed with ice water (5 mL). The solid was dried under reduced pressure to yield 0.47 g (74%) of N-hydroxy-3-methylisonicotinimidamide INT-69 as a white powder. LCMS-ESI (m/z) calculated for C7H9N3O: 151.2; found 152.1 [M+H]+, tR=0.56 min. 1H NMR (400 MHz, CD3OD) δ 8.43-8.32 (m, 2H), 7.34 (d, J=5.0, 1H), 2.39 (s, 3H).

1. customPrepared
2. temperatureOnce cooled to room temperature
3. filtrationthe reaction mixture was filtered
4. washto rinse the filter cake
5. concentrationThe filtrate was concentrated under reduced pressure
6. customThe resulting pale yellow solid was triturated with ice water (50 mL)
7. filtrationfiltered
8. washthe solid was washed with ice water (5 mL)
9. customThe solid was dried under reduced pressure

ORD record

ord-1d3ab01474064df2bd66b197a953c4eb

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394264B2