Water → HCID 22260720, compound

HRID 503178Notes

Reaction equation

HRID 503178 reaction equation
[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=O)[C:5](F)=[CH:6][CH:7]=1.O.[NH2:24][NH2:25].O>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:25][N:24]=[C:9]2[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 22260893HCID 22260893, compound

Product 1

HCID 22260720HCID 22260720, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A total of 1.63 g of (3-bromo-6-fluoro-2-methoxy-phenyl)-naphthalen-2-yl-methanone was dissolved in 15 ml of pyridine, 2.2 ml of hydrazine monohydrate was added, followed by stirring at 100° C. for 6 hours. Water was added to the reaction mixture, and then it was extracted with ethyl acetate for two times. The organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was removed by distillation. Then, the resulting crystals were washed with hexane once and dried in vacuo, to give 0.923 g of the title compound as brown crystals.

Workup

  1. extractionit was extracted with ethyl acetate for two times
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation
  5. washThen, the resulting crystals were washed with hexane once
  6. customdried in vacuo

Sources & evidence

ORD record
ord-37a08e6310a5486bb53a1a7424010f0c
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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