Sodium Carbonate → Methyl 4-[(3-amino-1H-pyrazol-1-yl)methyl]benzoate

HRID 1889178Notes

Reaction equation

HRID 1889178 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[N:12]2)=[CH:6][CH:5]=1.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[CH:14][C:13]([NH2:16])=[N:12]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 615448Methyl 4-((3-nitro-1H-pyrazol-1-yl)methyl)benzoate

Product 1

HCID 54920827Methyl 4-[(3-amino-1H-pyrazol-1-yl)methyl]benzoateYield 102.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Nitro-pyrazol-1-ylmethyl)-benzoic acid methyl ester (530 mg, 2.03 mmol) was dissolved in ethyl acetate (10 ml). Tin(II) chloride dihydrate (2.29 gm, 10.15 mmol) was added, reaction mixture was heated at 70 deg C. for 1 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 8-9 by addition of aq. saturated sodium carbonate and extracted with ethyl acetate (3×25 ml), dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide 4-(3-amino-pyrazol-1-ylmethyl)-benzoic acid methyl ester (480 mg).

Workup

  1. customreaction mixture
  2. temperaturewas heated at 70 deg C
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8b034c3e15649b8931ea7a3b2bbbc81
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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