Hydrazine hydrate (1:1) → 4-Hydrazinyl-2-Methylquinoline

HRID 1514813Notes

Reaction equation

HRID 1514813 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.O.[NH2:14][NH2:15]>C(O)C>[NH:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 779734-Chloro-2-methylquinoline

Product 1

HCID 20633884-Hydrazinyl-2-Methylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-2-methylquinoline (5.01 g, 28.2 mmol) and 80% hydrazine hydrate (8 ml) solution was refluxed in ethanol (30 mL) for 8 h. The resulting solution was cooled to room temperature and the solid formed was collected by filtration, washed with ethanol, and dried to yield known 4-hydrazino-2-methylquinoline,54,55 4.712 g (79.70%); mp 195-197° C.; 1H NMR (DMSO-d6) δ 2.64 (3H, s, Me), 5.15 (2H, brs, exchangeable, NH2), 6.99 (1H, s, ArH), 7.58 (1H, t, J=7.6 Hz, ArH), 7.86 (1H, t, J=7.6 Hz, ArH), 7.85 (1H, d, J=8.4 Hz, ArH), 8.42 (1H, d, J=8.2 Hz, ArH), 10.64 (1H, s, exchangeable, NH), Anal. Calcd. for (C10H12N3.HCl): C, 57.28; H, 5.77; N, 20.04. Found: C, 57.28; H, 5.77; N, 20.04.

Workup

  1. customthe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with ethanol
  4. customdried
  5. customto yield

Sources & evidence

ORD record
ord-5ac2271f4b9c49fe9f0bf1df6e33c515
Source dataset
uspto-grants-2012_07
Patent number
US08222297B2

Reaction notes

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