Hydrazine hydrate (1:1) → 6-Chloro-4-(isopropylamino)nicotinohydrazide

HRID 595391

Reaktionsgleichung

Reaktionsgleichung von HRID 595391
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]2[CH2:17]C[CH2:15]2)[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.O.[NH2:19][NH2:20]>C(O)C>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]([CH3:17])[CH3:15])[C:5]([C:6]([NH:19][NH2:20])=[O:7])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 89689654Ethyl 6-chloro-4-(cyclobutylamino)nicotinate

Produkt 1

HCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of ethyl 6-chloro-4-(isopropylamino)nicotinate (2) (3 g, 12.39 mmol) in ethanol (10 mL), hydrazine hydrate (3 mL) was added and refluxed at 80° C. for 3 h. The reaction mixture was cooled and concentrated to obtain crude compound. The residue obtained was triturated with diethyl ether and hexane and filtered to get solid, 6-chloro-4-(isopropylamino)nicotinohydrazide (10). LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.58 min; LCMS (ES-API), m/z 229.6 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customto obtain crude compound
  4. customThe residue obtained
  5. customwas triturated with diethyl ether and hexane
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f3b9b8900fb1460981cf6dfb90da552b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242975B2

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