Ethyl Acetoacetate → HCID 178429268, compound

HRID 878480Notes

Reaction equation

HRID 878480 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][N:4]=1)[NH2:2].O=[C:13]([CH3:20])[CH2:14][C:15](OCC)=[O:16]>CC(O)=O>[OH:16][C:15]1[N:1]([C:3]2[CH:8]=[C:7]([CH:6]=[CH:5][N:4]=2)[C:9]([OH:11])=[O:10])[N:2]=[C:13]([CH3:20])[CH:14]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 269672462-Hydrazinylpyridine-4-carboxylic acid

Product 1

HCID 178429268HCID 178429268, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-hydrazinylpyridine-4-carboxylic acid (306 mg, 2 mmol, PREPARATION 1) and ethyl 3-oxobutanoate (390 mg, 3 mmol) in AcOH (5 mL) was stirred at 100° C. overnight. The reaction mixture was cooled, concentrated, and purified by prep-HPLC to afford the title compound (72 mg, 16%) as yellow solid. 1H NMR (400 MHz, CD3OD): δ 2.72 (3H, s), 4.86 (1H, s), 7.71 (1H, d, J=4.8 Hz), 8.55 (1H, d J=4.8 Hz), 8.81 (1H, s). [M+H] Calc'd for C10H9N3O3, 220; Found, 220.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-ef45def7f2fd49e1b2a902f9b48e09a9
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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