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Hydrazine hydrate (1:1) → 6-phenoxy-3-styryl-4,5-dihydro-1H-indazole

HRID 1861066
Notes
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Reaction equation

HRID 1861066 reaction equation
[O:1]([C:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10](=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:26][NH2:27]>CC(O)=O.CCO>[O:1]([C:8]1[CH2:13][CH2:12][C:11]2[C:14]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:26][NH:27][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 693717203-Phenoxy-6-(3-phenyl-acryloyl)cyclohex-2-enone

Product 1

HCID 693704076-phenoxy-3-styryl-4,5-dihydro-1H-indazoleYield 36.4%

Reagents, catalysts & solvents 1

HCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-phenoxy-6-(3-phenyl-acryloyl)-cyclohex-2-enone (1.13 g, 3.55 mmol) in 20 mL of HOAc/EtOH (1:1) was added hydrazine monohydrate (0.21 mL, 4.3 mmol). The reaction was heated at 70° C. for 3 h, cooled and poured cautiously into saturated Na HCO3 solution and extracted with EtOAc (2×). The combined organic layers were washed with saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1) to give 6-phenoxy-3-styryl-4,5-dihydro-1H-indazole (3) as an off-white solid (406 mg, 36%): 1H NMR (DMSO-d6) δ 2.64 (t, 2H, J=8.0 Hz), 2.95 (t, 2H, J=8.0 Hz), 5.46 (s, 1H), 7.04 (AB, 2H, J=16.8 Hz), 7.15 (d, 2H, J=8.1 Hz), 7.25 (m, 2H), 7.42 (m, 4H), 7.55 (d, 2H, J=7.7 Hz), 12.44 (s, 1H). Anal. Calc. for C2H18N2O.0.2H2O: C, 79.32; H, 5.83, N, 8.81. Found: C, 79.36; H, 5.85; N, 8.84.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting hexanes/EtOAc (2:1)

Sources & evidence

ORD record
ord-2f6c9428ce2845469d398ec856a2c651
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06531491B1

Reaction notes

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