Hydrazine hydrate (1:1) → 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

HRID 850182Notes

Reaction equation

HRID 850182 reaction equation
[Cl:1][C:2]1[C:28]([N:29]([CH3:44])[C:30](=[O:43])[CH2:31][N:32]2C(=O)C3=CC=CC=C3C2=O)=[CH:27][CH:26]=[C:25]([Cl:45])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.O.NN>C(O)C>[NH2:32][CH2:31][C:30]([N:29]([C:28]1[C:2]([Cl:1])=[C:3]([C:25]([Cl:45])=[CH:26][CH:27]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH3:44])=[O:43]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 232920178-[2,6-dichloro-3-[N-methyl-N-(phthalimidoacetyl)amino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

Product 1

HCID 232920198-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinolineYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-[2,6-dichloro-3-[N-methyl-N-(phthalimidoacetyl)amino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (750 mg), hydrazine monohydrate (117 mg) and ethanol was heated under reflex for 4 hours. The precipitate was removed by filtration and filtrate was evaporated in vacua. The residue was dissolved with a mixture of chloroform and methanol (10:1, V/V), precipitate was removed by filtration and filtrate was evaporated in vacua. The residue was purified by column chromatography on silica gel eluting with chloroform--methanol to afford 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (390 mg) as an amorphous powder.

Workup

  1. temperaturewas heated under reflex for 4 hours
  2. customThe precipitate was removed by filtration and filtrate
  3. customwas evaporated in vacua
  4. dissolutionThe residue was dissolved with a mixture of chloroform and methanol (10:1, V/V), precipitate
  5. customwas removed by filtration and filtrate
  6. customwas evaporated in vacua
  7. customThe residue was purified by column chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-9a788ded8c3f42cc8bdb0f54c8fc923d
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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