Methanol → HCID 178499180, compound

HRID 720683Notes

Reaction equation

HRID 720683 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl.[CH3:13]N(C)CCCN=C=NCC.CO>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][O:10][C:9]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524956HCID 178524956, compound

Product 1

HCID 178499180HCID 178499180, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid (2.0 g, 12.7 mmol) in dichloromethane at 25° C. was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.68 g, 14.0 mmol), methanol (8.2 mL), and 4-dimethylaminopyridine (155 mg, 1.27 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with dichloromethane and was washed with a 1N aqueous hydrochloric acid solution (1×50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 45:55 ethyl acetate/petroleum ether) afforded 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.06 g, 48.8%) as a white solid: LR-MS for C5H5N3O4 (M−H)+ at m/z=170.

Workup

  1. washwas washed with a 1N aqueous hydrochloric acid solution (1×50 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05933b3896b94e9f8daefbab29fcf6e2
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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