Hydrochloric Acid → HCID 178431788, compound

HRID 1482059Notes

Reaction equation

HRID 1482059 reaction equation
[CH3:1][CH:2]([C:8](=O)[CH3:9])[C:3]([O:5]CC)=O.[C:11]([CH2:13][C:14]([NH2:16])=[O:15])#[N:12].[OH-].[K+].Cl>CO>[OH:15][C:14]1[N:16]=[C:3]([OH:5])[C:2]([CH3:1])=[C:8]([CH3:9])[C:13]=1[C:11]#[N:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 7898CyanoacetamideHCID 14797Potassium Hydroxide

Product 1

HCID 178431788HCID 178431788, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of ethyl 2-methyl-3-oxobutanoate (10 g, 69.4 mmol, 1 equiv) and 2-cyanoacetamide (5.8 g, 69.4 mmol, 1 equiv) was slowly added a solution of KOH (4.9 g, 87 mmol, 1.25 equiv) in MeOH (35 mL). Stir for 1 h during which time solution became homogenous yellow before developing a cream colored precipitate. Heat at reflux for 3 h. Upon cooling to ambient temperature, concentrated HCl (9 mL) was added. The off white solid was filtered and washed with ether to provide the product (10.7 g, 94%) as a cream colored solid. 1H NMR (500 MHz, DMSO-d6) δ 2.22 (s, 3H), 1.90 (s, 3H); LCMS (ESI, M+1): 165.05.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 h
  3. filtrationThe off white solid was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-29fe0af7a9844811a995a583eab9c977
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…