Hydrazine → 4-[4-(Pyrimidin-4-yl)phenoxy]butaneamine

HRID 1417319Notes

Reaction equation

HRID 1417319 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9][CH:8]=2)=[N:3][CH:2]=1.NN>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:9][CH:8]=2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 675995062-[4-[4-(Pyrimidin-4-yl)phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 570038714-[4-(Pyrimidin-4-yl)phenoxy]butaneamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4.6 g of 2-[4-[4-(pyrimidin-4-yl)phenoxy]butyl]-1H-isoindole-1,3(2H)-dione (Example 45) in 200 ml of boiling ethanol is treated with 0.8 ml of anhydrous hydrazine, and the mixture then refluxed for 9 hours. The hot suspension is filtered. The precipitate is washed with 125 ml of 1.5N HCl. The combined HCl and ethanolic filtrates are taken to dryness in vacuo to obtain the hydrochloride salt of the title compound. Mass spectrometry shows the residue to be the tide compound and the salt is utilized for synthesis without further purification, m.p. 208°-210° C. (dec.).

Workup

  1. temperaturethe mixture then refluxed for 9 hours
  2. filtrationThe hot suspension is filtered
  3. washThe precipitate is washed with 125 ml of 1.5N HCl

Sources & evidence

ORD record
ord-2a4a9a4523f744ea90afb3c6493af70e
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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