Ethanol → HCID 21537861, compound

HRID 1076682Notes

Reaction equation

HRID 1076682 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH:8]1([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH2:12])[CH2:10][CH2:9]1.C(Cl)(=O)C1C=C[N:22]=[CH:21][CH:20]=1.C([OH:29])C>>[CH:8]1([C:11]2([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[O:29][N:22]=[C:21]([C:20]3[CH:5]=[CH:4][N:3]=[CH:6][CH:7]=3)[CH2:12]2)[CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 21537869HCID 21537869, compound

Product 1

HCID 21537861HCID 21537861, compound

Procedure

To a stirred solution of 60 g. of triethylamine and 88 g. of 1-(1-cyclopropylvinyl)-pyrrolidine in 750 ml. of ethanol is added 40.5 g. of isonicotinoyl chloride, oxime hydrochloride in small portions during 100 minutes at room temperature. The ethanol is evaporated under reduced pressure and the oily residue is mixed with water. The aqueous mixture is extracted with ether, the ethereal solution dried over sodium sulfate and concentrated under reduced pressure to yield a brown solid, which is recrystallized from benzene-hexane to furnish straw-colored crystals, melting point 80°-85°C.

Workup

  1. customThe ethanol is evaporated under reduced pressure
  2. additionthe oily residue is mixed with water
  3. extractionThe aqueous mixture is extracted with ether
  4. dry with materialthe ethereal solution dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a brown solid, which
  7. customis recrystallized from benzene-hexane
  8. customto furnish straw-colored crystals, melting point 80°-85°C.

Sources & evidence

ORD record
ord-6c879b55c8c047b1a7538d3decd172d9
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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