Ethyl Acetate → HCID 54000152, compound

HRID 728197Notes

Reaction equation

HRID 728197 reaction equation
Br[CH2:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(OCC)(=O)C>C(#N)C>[CH2:16]([O:15][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]2[N:24]=[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]3[CH:2]=2)[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 54537144HCID 54537144, compound

Product 1

HCID 54000152HCID 54000152, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromo-1-(3-benzyloxy-4-nitrophenyl)but-1-en-3-one (55.0 g) and 2-aminopyridine (42.3 g) in acetonitrile (380 ml) was stirred for 4 hours at ambient temperature. Ethyl acetate was added to the reaction mixture and the precipitate was collected by filtration. A mixture of water and ethyl acetate was added to the precipitate and the mixture was adjusted to pH 7.0 with 20% potassium carbonate. The precipitate was collected by filtration and washed with water to give 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]imidazo[1,2-a]pyridine (40.1 g).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. additionA mixture of water and ethyl acetate
  3. additionwas added to the precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-6a61493a0bdf4c7ea24996aa53d0ccce
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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