Hydrochloric Acid → Methyl 5-isopropyl-4-nitropyrazol-3-carboxylate

HRID 19588Notes

Reaction equation

HRID 19588 reaction equation
[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].Cl.[CH3:16]O>>[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:16])=[O:10])[C:5]=1[N+:12]([O-:14])=[O:13])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 121506014-nitro-5-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 12150602Methyl 5-isopropyl-4-nitropyrazol-3-carboxylateYield 91%

Conditions

Temperature
60 °C

Procedure

5-Isopropyl-4-nitropyrazole-3-carboxylic acid was added to a 4.5M solution of HCl in absolute methanol. The reaction mixture was heated at 60° C. for 7 hours. The title compound was crystallized from ethyl acetate; yield 91%; mp=78-80° C. 1H NMR (300 MHz, CDCl3): 1.39 d (6H, J=7.1 Hz); 3.64 sept (1H, J=7.1 Hz), 3.98 s (3H). CHN required: C=45.07%; H=5.20%; N=19.70%; found: C=45.21%; H=5.23%; N=19.65%.

Workup

  1. customThe title compound was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-99e2a19f95d54763b54daf0156cff5bb
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Reaction notes

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