Hydrazine hydrate (1:1) → 8-[3-(N-glycyl-N-methylamino)2,6-dichlorobenzyloxy]-2-methylquinoline

HRID 564930Notes

Reaction equation

HRID 564930 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:36])[CH2:24][N:25]2C(=O)C3=CC=CC=C3C2=O)[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:37])[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]=[CH:11]2.O.NN>C(O)C>[NH2:25][CH2:24][C:23]([N:21]([C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:37])=[CH:18][CH:19]=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]=[CH:11]2)[CH3:22])=[O:36]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118004498-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-2-methylquinoline

Product 1

HCID 117954848-[3-(N-glycyl-N-methylamino)2,6-dichlorobenzyloxy]-2-methylquinolineYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-[2,6-dichloro-3-[N-(phthalimido-acetyl)-N-methylamino]benzyloxy)-2-methylquinoline (3.98 g), hydrazine monohydrate (0.72 ml) and ethanol (40 ml) was heated under reflux for 1 hour. The precipitate was removed by vacuum filtration and the filtrate was evaporated in vacuo. The residue was dissolved with dichloromethane and the precipitate was removed by vacuum filtration. The filtrate was evaporated in vacuo to give 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy)-2-methylquinoline (2.99 g) as a yellow amorphous powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe precipitate was removed by vacuum filtration
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved with dichloromethane
  6. customthe precipitate was removed by vacuum filtration
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-068f573c6abd48c9a15e8a9051ff359c
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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