Pyridine → 914094-82-9

HRID 910755Notes

Reaction equation

HRID 910755 reaction equation
[C:1](Cl)([O:3][CH2:4][CH:5]=[CH2:6])=[O:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.N1C=CC=CC=1>ClCCl>[CH2:4]([O:3][C:1](=[O:2])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 693314-Aminobenzyl alcohol

Product 1

HCID 64795250914094-82-9Yield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Alloc-Cl (537 g) in dichloromethane (5 ml) was added dropwise to a solution of (4-amino-phenyl)-methanol (500 mg) and pyridine (5 ml) in dichloromethane (5 ml). After stirring for 2 h, the reaction mixture was diluted with dichloromethane and washed with water. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The title compound (243 mg) was obtained by recrystallization from dichloromethane. The mother liquor was chromatographed on silica gel in heptane/ethyl acetate=1/1 (v/v) as eluent which yielded another 245 mg of the title compound. Yield: 488 mg.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a59ebdd299764efdbc4ee62f373048d0
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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