Hydroxyamine hydrochloride → HCID 96133985, Verbindung

HRID 1752651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752651
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl.[NH2:14][OH:15].C(=O)(O)[O-].[Na+]>CO>[OH:15][N:14]=[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[N:3]=[CH:4]2)[NH2:12]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 105830411-Methyl-1H-indazole-5-carbonitrile

Produkt 1

HCID 96133985HCID 96133985, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-methyl-1H-indazole-5-carbonitrile (205 mg, 1.304 mmol), hydroxylamine hydrochloride (363 mg, 5.22 mmol) and sodium bicarbonate (548 mg, 6.52 mmol) in Methanol (6 mL) was heated to 60 degrees for 90 min. The reaction mixture was cooled to ambient temperature and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organics washed with brine, dried (Na2SO4) and concentrated to afford the crude N′-hydroxy-1-methyl-1H-indazole-5-carboximidamide (174 mg, 0.915 mmol, 70% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15-1.38 (m, 6H) 2.13 (s, 3H) 4.18 (dq, J=19.59, 7.15 Hz, 4H) 4.98 (br. s., 1H) 8.90 (br. s., 1H). LC/MS (m/z) ES+=191 (M+1).

Aufarbeitung

  1. custompartitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ca46f6592b4c4a6a8a20ad9679b01fbb
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163023B2

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