Hydrazine hydrate (1:1) → 4-(7-Methoxy-indan-4-yloxy)-3,5-dimethyl-1H-pyrazole

HRID 389297Notes

Reaction equation

HRID 389297 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([OH:14])=[CH:7][CH:6]=1.Cl[CH:16]([C:20](=O)[CH3:21])[C:17](=O)[CH3:18].[Br-].[K+].O.[NH2:26][NH2:27]>O1CCCC1.C(O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][C:16]2[C:20]([CH3:21])=[N:26][NH:27][C:17]=2[CH3:18])=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2

Participants

9

Reactant 5

HCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 743283-Chloro-2,4-pentanedioneHCID 253877Potassium BromideHCID 206091567-methoxy-2,3-dihydro-1H-inden-4-ol

Product 1

HCID 668124664-(7-Methoxy-indan-4-yloxy)-3,5-dimethyl-1H-pyrazoleYield 18.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To the suspension of 60% Sodium hydride (2.0 gm, 0.051 moles) in Tetrahydrofuran (20 ml) added a solution of 7-Methoxyindan-4-ol (7.0 gm, 0.042 mole) in Tetrahydrofuran (30 ml) at room temperature. After one hour stirring a solution of 3-Chloro 2,4-pentanedione (9.0 ml, 0.075 mole) in Tetrahydrofuran (20 ml) was added followed by addition of Potassium bromide (3.0 gm, 0.025 mole). The reaction mixture was stirred at 70° C. for 6 hours. The water was added and extracted with Diethyl ether. The Ether layer was separated and distilled off to give an oily mass which was partially purified through a column using 2% Ethyl acetate in Hexane to give crude mass (2.7 gm). The obtained crude mass was stirred with Hydrazine hydrate (1 ml) in 20 ml Ethanol at 10° C. Ethanol was evaporated to dryness. The obtained residue was partitioned between water and Ethyl acetate. The separated Ethyl acetate layer was dried over Sodium sulphate and distilled off to give desired product (2.0 gm).

Workup

  1. additionwas added
  2. extractionextracted with Diethyl ether
  3. customThe Ether layer was separated
  4. distillationdistilled off
  5. customto give an oily mass which
  6. customwas partially purified through a column
  7. customto give crude mass (2.7 gm)
  8. customThe obtained crude mass
  9. customEthanol was evaporated to dryness
  10. customThe obtained residue was partitioned between water and Ethyl acetate
  11. dry with materialThe separated Ethyl acetate layer was dried over Sodium sulphate
  12. distillationdistilled off

Sources & evidence

ORD record
ord-534f0f0292be476ca65b04164d4f7fa2
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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