Hydrazine hydrate (1:1) → 8-Amino-3-butyryl-4-(2-methylphenylamino)quinoline

HRID 1090672Notes

Reaction equation

HRID 1090672 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[N:24]1C(=O)C2=CC=CC=C2C1=O)(=[O:5])[CH2:2][CH2:3][CH3:4].O.NN>C(O)C>[NH2:24][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[C:15]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 104788903-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline

Product 1

HCID 102454028-Amino-3-butyryl-4-(2-methylphenylamino)quinolineYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline (9.0 g, 0.02 moles) and hydrazine hydrate (1.5 ml) were heated together under reflux in ethanol (100 ml) for 2 hours. The solvent was evaporated and the residue was stirred in chloroform, filtered and the filtrate concentrated and chromatographed (silica gel chloroform) to give 8-amino-3-butyryl-4-(2-methylphenylamino)quinoline (5.5 g, 86%), as a bright yellow oil which crystallized on standing, m.p. 108°-10° C.

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. customchromatographed (silica gel chloroform)

Sources & evidence

ORD record
ord-4e314486afe64667800b0843719095df
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

Loading…