Nitric Acid → 4-nitro-5-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

HRID 19586Notes

Reaction equation

HRID 19586 reaction equation
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)([CH3:3])[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[C:5]=1[N+:12]([O-:14])=[O:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7764215-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 121506014-nitro-5-(propan-2-yl)-1H-pyrazole-3-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To an ice-cooled and stirred solution of 2.9 g (18.8 mmol) 5-isopropylpyrazol-3-carboxylic acid II (lit.: Baraldi P. G. et al: Farmaco, 46, 1337 (1991); mp=136-140° C.) in fuming sulphuric acid (65%) the nitric acid (65%) was added portion wise. The stirring was continued for 1 h at room temperature and then another 3 h at 104° C. temperature and then poured into ice-water. The white precipitate of product was filtered and crystallized from water; (yield 76%); mp=139-142° C.; 1H NMR (300 MHz, DMSO): 1.22 d (6H, 7.1 Hz), 2.94 sept (1H, 7.1 Hz), 3.33 s (1H), 6.45 bs (1H); CHN required: C=42.02%; H=4.56%; N=21.09; found: C=42.41%; H=4.49%; N=21.01%.

Workup

  1. additionwas added portion wise
  2. filtrationThe white precipitate of product was filtered
  3. customcrystallized from water

Sources & evidence

ORD record
ord-d270c0d49cf0474cb69dc63e0608a436
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Reaction notes

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