Hydrochloric Acid → HCID 178524750, compound

HRID 1470313Notes

Reaction equation

HRID 1470313 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:10])=[NH:9].C[O-].[Na+].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21]CC)=[O:20])C.[OH-].[K+].Cl>CO.O>[OH:16][C:17]1[C:18]([C:19]([OH:21])=[O:20])=[CH:24][N:10]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[N:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 12403615Pyridine-2-carboximidamide hydrochloride

Product 1

HCID 178524750HCID 178524750, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To picolinamidine hydrochloride (10-b) (112 g, 0.71 mol) in MeOH (1.1 L) was added sodium methoxide (39.4 g, 0.71 mol) and diethyl ethoxymethylenemalonate (2-b) (142 g, 0.71 mol). The reaction was heated at reflux overnight and then cooled to room temperature. The resulting mixture was filtered and to the filtrate was added potassium hydroxide (71.4 g, 1.37 mol) in water (265 mL). The reaction was heated at reflux for 2 h. The reaction mixture was cooled to room temperature before adding conc. HCl (37%, 180 mL, 2.35 mol) in portions. The reaction aged for 2 h. The solids were filtered and rinsed with EtOH, Et2O and then hexane to provide compound 10-c (110 g, 65%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationThe resulting mixture was filtered and to the filtrate
  4. temperatureThe reaction was heated
  5. temperatureat reflux for 2 h
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customThe reaction aged for 2 h
  8. filtrationThe solids were filtered
  9. washrinsed with EtOH, Et2O

Sources & evidence

ORD record
ord-fdbba90c3df54f728697490f86fa9d14
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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