Hydrazine hydrate (1:1) → HCID 136049266, compound

HRID 1296924Notes

Reaction equation

HRID 1296924 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:13])=[C:6]([C:14]1[CH:25]=[CH:24][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])=[CH:16][CH:15]=1)[C:5]2=O.O.[NH2:28][NH2:29]>>[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[C:6]([C:14]3[CH:25]=[CH:24][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])=[CH:16][CH:15]=3)=[C:7]([CH3:13])[NH:29][N:28]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58913571HCID 58913571, compound

Product 1

HCID 136049266HCID 136049266, compoundYield 31.5%

Procedure

This compound was synthesised in the same manner as described above. 4-[4-(6-Chloro-7-hydroxy-2-methyl-4-oxo-4H-chromen-3-yl)-phenoxy]-butyronitrile (0.55, 1.49 mmol), hydrazine hydrate (6 ml). The quenched reaction was extracted into ethyl acetate, washed (water), dried (MgSO4), and the solvent removed under vacuum to give a brown oil which was purified by column chromatography to give 4-{4-[3-(5-Chloro-2,4-dihydroxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-phenoxy}-butyronitrile as a white solid (0.18 g, 31.5%); Rf 0.5 Ethyl acetate/Hexane (70/30).

Workup

  1. customThis compound was synthesised in the same manner
  2. customThe quenched reaction
  3. extractionwas extracted into ethyl acetate
  4. washwashed (water)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under vacuum
  7. customto give a brown oil which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-56e09b77289c41b994fad24356eb604e
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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