Diethyl Ether → HCID 178487891, compound

HRID 1767038Notes

Reaction equation

HRID 1767038 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 (6.26 g, 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-fb4f0e5b3de2437d9ec632097731500e
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

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