Ethanol → HCID 178488793, compound

HRID 1417537Notes

Reaction equation

HRID 1417537 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][N:13]=[N:12][C:11]2([CH3:18])[N+]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O.[OH-].[K+].C(O)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]([CH3:18])=[N:12][NH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 14797Potassium HydroxideHCID 54140188HCID 54140188, compound

Product 1

HCID 178488793HCID 178488793, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-bromo-4-methoxyphenyl)-3-methyl-3-nitro-4,5-dihydro-3H-pyrazole (100 mg, 0.32 mmol) and 0.5 mL of water was stirred at room temperature and 2.0 mL of 40% aqueous potassium hydroxide was added. After the mixture had been sonicated for 5 min, 1.0 mL of 95% ethanol was added, followed 20 min later by another 0.5 mL of 95% ethanol. After 15 min, the solution was extracted with 2×20 mL of ether. The ether extracts were washed in succession with 10 mL of saturated aqueous sodium chloride solution, dried (sodium sulfate), decanted, and evaporated to give a white solid. Flash column chromatography on 4 g of silica gel eluting with 15-20% ethyl acetate in dichloromethane gave 80 mg of white solid (94% yield). 1H NMR (400 MHz, CDCl3): δ 7.62 (s, 1H), 7.30 (dd, 1H, J=8, 2 Hz), 6.94 (d, 1H, J=8 Hz), 3.93 (s, 3H), 2,43 (s, 3H). Mass spectrum (NH3CI): m/e=267 (M+1).

Workup

  1. customAfter the mixture had been sonicated for 5 min
  2. extractionthe solution was extracted with 2×20 mL of ether
  3. washThe ether extracts were washed in succession with 10 mL of saturated aqueous sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. customdecanted
  6. customevaporated
  7. customto give a white solid

Sources & evidence

ORD record
ord-dc2b0f02e27948418315db9926ad1cbc
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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