Diethyl Ether → HCID 178487891, compound

HRID 1435841Notes

Reaction equation

HRID 1435841 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10](OC)(=[O:13])[C:11]#[CH:12].C(OCC)C>CO.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:13][C:10]1[C:7]2[C:2](=[CH:3][CH:4]=[C:5]([O:8][CH3:9])[N:6]=2)[N:1]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 13536Methyl propiolateHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 178487891HCID 178487891, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent2×

Procedure

5-Amino-2-methoxypyridine (55.0 g, 0.44 mole) in methanol (1000 mL) with methyl propiolate (40 mL, 0.44 mole) was stirred for 48 hours, then evaporated and the product purified by chromatography on-silica gel (dichloromethane) followed by recrystallization from dichloromethane-hexane (44.6 g, 48%). The unsaturated ester (10.5 g, 0.05 mole) in warm Dowtherm A (50 mL) was added over 3 minutes to refluxing Dowtherm A, and after a further 20 minutes at reflux the mixture was cooled and poured into diethyl ether. The precipitate was filtered to give a solid (6.26g, 70%).

Workup

  1. customevaporated
  2. customthe product purified by chromatography on-silica gel (dichloromethane)
  3. customfollowed by recrystallization from dichloromethane-hexane (44.6 g, 48%)
  4. temperatureafter a further 20 minutes at reflux the mixture
  5. temperaturewas cooled
  6. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-8c7ee6e7522f4af396cf86104c9e32dc
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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