Methanol → HCID 20511176, compound

HRID 1448956Notes

Reaction equation

HRID 1448956 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH3:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].CO>C(O)(=O)C>[CH3:1][N:2]([CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH3:5])[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 20351352HCID 20351352, compound

Product 1

HCID 20511176HCID 20511176, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

dl-4-(1-Methylaminoprop-2-yl)pyridine (4.5 g.) in acetic acid (15 ml.) was treated cautiously with acetic anhydride (10 ml.) followed by allowing the mixture to stand at ambient temperature overnight. Methanol (20 ml.) was then added to destroy excess acetic anhydride, followed by evaporation in vacuo (at 40° C.) to remove methanol and methyl acetate. The residue was diluted with water and treated portionwise with sodium carbonate (anhydrous) until alkaline (pH 10-12). The oily suspension was extracted with chloroform (3×60 ml.) and the bulked extracts were dried (Na2CO3) and evaporated to dryness in vacuo to give a near-colorless oil (6.8 g.). The oil was distilled to give pure dl-4-(1-[N-methylacetamido]prop-2-yl)pyridine (3 g.), b.p. 138°-140°/0.4 mm Hg. (as a colorless oil).

Workup

  1. customto destroy excess acetic anhydride
  2. customfollowed by evaporation in vacuo (at 40° C.)
  3. customto remove methanol and methyl acetate
  4. additionThe residue was diluted with water
  5. additiontreated portionwise with sodium carbonate (anhydrous) until alkaline (pH 10-12)
  6. extractionThe oily suspension was extracted with chloroform (3×60 ml.)
  7. dry with materialthe bulked extracts were dried (Na2CO3)
  8. customevaporated to dryness in vacuo
  9. customto give a near-colorless oil (6.8 g.)
  10. distillationThe oil was distilled

Sources & evidence

ORD record
ord-6438855a36ed4367ac3b644ab25778cd
Source dataset
uspto-grants-1980_02
Patent number
US04188391

Reaction notes

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