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

HRID 595391

Reaction equation

HRID 595391 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f3b9b8900fb1460981cf6dfb90da552b
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Linked notes

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