Ethyl Acetate → HCID 57496377, compound

HRID 1958441Notes

Reaction equation

HRID 1958441 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:7]=1[N+:21]([O-])=O)=[O:5])[CH3:2].C(OCC)(=O)C>[NH4+].[Cl-].[Zn]>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][CH:16]=2)[C:7]=1[NH2:21])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 57496378HCID 57496378, compound

Product 1

HCID 57496377HCID 57496377, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

3-(4-Methanesulfonyl-phenyl)-4-nitro-isoxazole-5-carboxylic acid ethyl ester (6.2 g) was suspended in sat. NH4Cl (100 mL) and treated with Zn (10.0 g) at room temperature. The reaction was stirred for 3 h and ethyl acetate (100 mL) was added. After stirring for 1 h, zinc was filtered off. The ethyl acetate was taken and washed with H2O, dried over MgSO4 and concentrated under vacuum to afford the crude product (4.3 g, 77%). The product was crystallized in ethyl acetate/hexane (1/3) to afford the desired compound. LCMS 311.1 [M+H].

Workup

  1. stirringAfter stirring for 1 h
  2. filtrationzinc was filtered off
  3. washwashed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product (4.3 g, 77%)
  7. customThe product was crystallized in ethyl acetate/hexane (1/3)

Sources & evidence

ORD record
ord-8b3cac281ab1494ebf8c858e0fd880e6
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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