Stannous chloride dihydrate → HCID 66584236, compound

HRID 2074145Notes

Reaction equation

HRID 2074145 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([N+:10]([O-])=O)[N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[N:6]=1)=[O:4].O.O.Cl[Sn]Cl>O(CCOC)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66584193HCID 66584193, compound

Product 1

HCID 66584236HCID 66584236, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-nitropyrazole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (3.2 g, 10.48 mmol) and SnCl2.2H2O (7.2 g, 31.9 mmol) in 1,2-dimethoxylethane (60 mL) was heated to reflux for 2 hours. The solvent was removed in vacuo. The residue was neutralized with saturated aqueous sodium carbonate. The resulting solution was filtered and the filtrate was extracted with ethyl acetate. The organic layer was separated and dried over anhydrous Na2SO4 and concentrated to give 5-aminopyrazole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (2.74 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.30-7.18 (m, 5H), 6.17 (s, 1H), 3.82 (s, 3H), 3.63 (s, br., 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. filtrationThe resulting solution was filtered
  5. extractionthe filtrate was extracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1aa48d4dad6a4ddb88dbe42e217bdc0e
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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