Sodium nitromalonaldehyde hydrate → HCID 178427406, compound

HRID 1943947Notes

Reaction equation

HRID 1943947 reaction equation
O.[Na].[N+:3]([CH:6]([CH:9]=O)[CH:7]=O)([O-:5])=[O:4].[NH2:11][C:12]1[N:16]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:15]=[C:14]([OH:27])[CH:13]=1.FC1(F)C[C@H]1C1C2C(=NC=C(NC(=O)C3C(F)=CC=C(NS(CCC)(=O)=O)C=3F)C=2)NN=1>C(O)(=O)C.O>[N+:3]([C:6]1[CH:7]=[C:13]2[C:14]([OH:27])=[N:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:12]2=[N:11][CH:9]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 71317419Sodium nitromalonaldehyde hydrateHCID 178427407HCID 178427407, compoundHCID 178461063HCID 178461063, compound

Product 1

HCID 178427406HCID 178427406, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Nitromalonaldehyde sodium salt monohydrate (3.57 g, 22.7 mmol) was added to suspension of 5-amino-1-tosyl-1H-pyrazol-3-ol (5.00 g, 19.7 mmol; see Elgemeie, Galal H., et al. “Novel Synthesis of 5-Amino-1-arylsulfonyl-4-pyrazolin-3-ones as a New Class of N-Sulfonylated Pyrazoles.” J. Chem. Res. (S). Issue 6 (1999): pp. 384-385) in acetic acid (30 mL). The mixture was heated at 50° C. for 4 hours. The partial suspension was allowed to cool and diluted with water. The resulting solid was collected by vacuum filtration and dried under high vacuum to afford 5-nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-ol (4.21 g, 12.6 mmol, 63.8% yield) as a solid.

Workup

  1. temperatureto cool
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8eefbc4964684a86a9f856bb44a582ca
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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