Hydrazine hydrate (1:1) → HCID 55281853, compound

HRID 1959590Notes

Reaction equation

HRID 1959590 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.O.[NH2:15][NH2:16]>O1CCOCC1>[NH:15]([C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)[NH2:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 55281853HCID 55281853, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-2-methyl-quinolin-8-ol (0.10 g, 0.51 mmol) and hydrazine monohydrate (0.75 mL, 15 mmol) in dioxane (10 mL) was heated to reflux for 4 d. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (elution with DCM/methanol/conc. aqueous NH3 5:1:0.033) to give the title compound. MS (m/z): 190.1 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 d
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography on silica gel (elution with DCM/methanol/conc. aqueous NH3 5:1:0.033)

Sources & evidence

ORD record
ord-f71735bd29264455af3433421cab84a7
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

Loading…