Dichloromethane → HCID 15572422, compound

HRID 443416Notes

Reaction equation

HRID 443416 reaction equation
Cl.[NH2:2][CH:3]([CH3:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1.[C:13](Cl)(=[O:15])[CH3:14].[C:17](=[O:20])(O)[O-].[Na+].[CH2:22](Cl)Cl>N1C=CC=CC=1>[C:13]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH:3]([NH:2][C:17](=[O:20])[CH3:22])[CH3:12])=[N:6][CH:7]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 23467157HCID 23467157, compound

Product 1

HCID 15572422HCID 15572422, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting material is prepared as follows: To the suspension of 1.01 g of 2-(2-aminopropyl)-5-pyridinol hydrochloride in 40 ml of methylene chloride, 3.3 ml of pyridine are added, followed by 1.47 g of acetyl chloride while stirring at room temperature. After 17 hours an equal volume of saturated aqueous sodium bicarbonate is added, the organic layer separated, dried and evaporated. The residual oil is chromatographed on silica, using methanolethyl acetate (4:1) as eluant, to yield the 5-acetoxy-2-(2-acetylaminopropyl)-pyridine, showing in the IR-spectrum peaks at 1758 and 1658 cm-1.

Workup

  1. customThe starting material is prepared
  2. additionare added
  3. customthe organic layer separated
  4. customdried
  5. customevaporated
  6. customThe residual oil is chromatographed on silica

Sources & evidence

ORD record
ord-12c7aaf3e9c346a9acb70b982a58f264
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

Loading…