Hydrazine hydrate (1:1) → 4-[4-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-methyl-1H-pyrazol-3-yl]-6-ethyl-1,3-benzenediol

HRID 1296923Notes

Reaction equation

HRID 1296923 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:20](=O)[C:19]4[C:14](=[CH:15][C:16]([OH:24])=[C:17]([CH2:22][CH3:23])[CH:18]=4)[O:13][C:12]=3[CH3:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.O.[NH2:27][NH2:28]>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:20]([C:19]4[CH:18]=[C:17]([CH2:22][CH3:23])[C:16]([OH:24])=[CH:15][C:14]=4[OH:13])=[N:27][NH:28][C:12]=3[CH3:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5399648HCID 5399648, compound

Product 1

HCID 9841704-[4-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-methyl-1H-pyrazol-3-yl]-6-ethyl-1,3-benzenediol

Procedure

This compounds was synthesised in the same manner as described above. 3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-ethyl-7-hydroxy-2-methyl-chromen-4-one (0.6 g, 1.77 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 yellow oil which was purified by column chromatography to give 4-[4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-5-methyl-1H-pyrazol-3-yl]-6-ethyl-benzene-1,3-diol as a clear oil which solidified over a period of 1 month (0.38 g, 60.9%); Rf 0.4 cf SM 0.6 Hexane/Ethyl acetate/MeOH (8/4/1).

Workup

  1. customThis compounds 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 yellow oil which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c089567320074ef58d7d32ef276a0bd0
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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