Hydroxyamine hydrochloride → 6-Bromo-2-methylpyrimidine-4-carbaldehyde oxime

HRID 572677

Reaktionsgleichung

Reaktionsgleichung von HRID 572677
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=O)[CH:3]=1.[NH2:11][OH:12].Cl.C([O-])(=O)C.C(O)(=O)C.[Na+]>C(O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=[N:11][OH:12])[CH:3]=1

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 23662384Sodium DiacetateHCID 866759296-Bromo-2-methylpyrimidine-4-carbaldehyde

Produkt 1

HCID 1364132336-Bromo-2-methylpyrimidine-4-carbaldehyde oximeAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 6-bromo-2-methylpyrimidine-4-carbaldehyde (11 g, 54.7 mmol, Preparation #17 step 1) and NH2OH.HCl (7.61 g, 109 mmol, Sisco Research Labs) in ethanol (75 mL) and water (25 mL) was added sodium acetate acetate (13.47 g, 164 mmol). The reaction mixture was heated to reflux at about 90° C. for about 1 h. The mixture was cooled to RT and diluted with water (200 mL). The separated product (solid) was collected by filtration, washed with water and dried under vacuum to afford 6-bromo-2-methylpyrimidine-4-carbaldehyde oxime 4.0 g (33.8%), 1H NMR (400 MHz, DMSO) δ: 12.43 (s, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 2.61 (s, 3H), MS m/z: 216 (negative mode).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureThe mixture was cooled to RT
  3. filtrationThe separated product (solid) was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9eb1ee3269684dae9f81e4efe5659cd3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029409B2

Verknüpfte Notizen

Wird geladen…