Hydrazine hydrate (1:1) → Quinoline-2-carbohydrazide

HRID 539649Notes

Reaction equation

HRID 539649 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13]C)=O.O.[NH2:16][NH2:17]>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:16][NH2:17])=[O:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 421738methyl quinoline-2-carboxylate

Product 1

HCID 246466Quinoline-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl quinoline-2-carboxylate 3.2 (10.1 g, 0.054 mol) was dissolved in 50 mL of ethanol and hydrazine hydrate (8.1 g, 0.16 mol) was added. The mixture was heated to reflux for 1 h and cooled down to RT at which point a precipitate formed. The mixture was concentrated to approximately ⅓ of the volume and the precipitate was filtered off, washed with small volumes of ethanol to afford intermediate 2a solvated by ½ equivalent of ethanol. Yield 10 g (99%). 1HNMR (DMSO-d6): δ: 9.95 ppm (s, 1H), 8.55 (d, 1H), 8.1 ppm (d, 2H), 8.05 ppm (d, 1H), 8.85 ppm (t, 1H), 7.65 ppm (t, 1H), 4.6 ppm (s, 2H), 4.3 ppm (t, 0.5H), 4.4 ppm (q, 1H), 1.05 ppm (q, 1.5H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customformed
  4. concentrationThe mixture was concentrated to approximately ⅓ of the volume
  5. filtrationthe precipitate was filtered off
  6. washwashed with small volumes of ethanol

Sources & evidence

ORD record
ord-00f4b099eb224f0b8d4e65d43977171f
Source dataset
uspto-grants-2014_10
Patent number
US08871761B2

Reaction notes

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