Methanol → HCID 178499180, compound

HRID 1426277Notes

Reaction equation

HRID 1426277 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[C:10]([C:14]([OH:16])=[O:15])=[N:11][NH:12][CH:13]=1)([O-:8])=[O:7].[CH3:17]O>>[N+:6]([C:9]1[C:10]([C:14]([O:16][CH3:17])=[O:15])=[N:11][NH:12][CH:13]=1)([O-:8])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524956HCID 178524956, compound

Product 1

HCID 178499180HCID 178499180, compound

Procedure

Fuming sulfuric acid (4 mL) was added to a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (16.0 g, 102 mmol) in methanol (200 mL), and the reaction was stirred at RT for 24 hours. The reaction mixture was concentrated, and the resulting solid was partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, providing C29 as a white solid. Yield: 17.1 g, 99.9 mmol, 98%. LCMS m/z 170.0 (M−1). 1H NMR (400 MHz, CDCl3) δ 4.05 (s, 3H), 8.40 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting solid was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customproviding C29 as a white solid

Sources & evidence

ORD record
ord-ce6cd2a637464a1fab92627973163988
Source dataset
uspto-grants-2015_01
Patent number
US08933095B2

Reaction notes

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