Hydrazine hydrate (1:1) → HCID 18704968, compound

HRID 2287461Notes

Reaction equation

HRID 2287461 reaction equation
[Cl:1][C:2]1[C:25]([N:26]([C:28](=[O:41])[CH2:29][N:30]2C(=O)C3=CC=CC=C3C2=O)[CH3:27])=[CH:24][CH:23]=[C:22]([Cl:42])[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[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.O.NN>C(O)C>[NH2:30][CH2:29][C:28]([N:26]([C:25]1[C:2]([Cl:1])=[C:3]([C:22]([Cl:42])=[CH:23][CH:24]=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[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[CH3:27])=[O:41]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54006413HCID 54006413, compound

Product 1

HCID 18704968HCID 18704968, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 8-[2,6-dichloro-3-(N-phthalimidoacetyl-N-methylamino)benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (1.91 g) in ethanol (19 ml) was added hydrazine monohydrate (318 mg), and the mixture was refluxed for 1 hour. After cooling, the resulting precipitates was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in chloroform. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was pulverized with diisopropyl ether to give 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (1.5 g) as colorless amorphous.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe resulting precipitates
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionthe residue was dissolved in chloroform
  7. filtrationInsoluble material was filtered off
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-523d7fbeaedc4692a5f5ff34028039f2
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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