Hydrazine hydrate (1:1) → 5-[4-(3-Amino-propoxy)-phenyl]-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

HRID 728905Notes

Reaction equation

HRID 728905 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([C:24]#[N:25])[C:19](=[O:23])[NH:20][C:21]=3[CH3:22])=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[C:18]([C:24]#[N:25])[C:19](=[O:23])[NH:20][C:21]=2[CH3:22])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 543645795-(4-Phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile

Product 1

HCID 116448765-[4-(3-Amino-propoxy)-phenyl]-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrileYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.885 g (4.70 mmol) of 5-(4-phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile and 251 μl (5.17 mmol) of hydrazine monohydrate in 50 ml of ethanol is heated 16 hr at reflux. The volatiles are removed under vacuum and the residue is taken up in 15 ml of 1:1 CHCl3 :CH3 and flashchromatographed through a 6 inch length column of silica gel (90:10:2 CHCl3 :CH3OH:NH4OH). The solid obtained form the chromatography is recrystallized from CHCl3 :CH3OH to give 901 mg of 5-(4-aminopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile as a yellow powder. 1H-NMR (d6 -DMSO): δ 1.80 (t,2H); 2.73 (t,2H); 3.70 (s broad, 2H); 4.03 (t,2H); 6.92 (d,2H); 7.20 (d,2H); 7.85 (s, 1H).

Workup

  1. temperatureat reflux
  2. customThe volatiles are removed under vacuum
  3. customThe solid obtained form the chromatography
  4. customis recrystallized from CHCl3

Sources & evidence

ORD record
ord-4daf87a5cae44349a6e6c6572570719c
Source dataset
uspto-grants-1991_09
Patent number
US05051431

Reaction notes

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