Pyridine → HCID 870083, compound

HRID 840117Notes

Reaction equation

HRID 840117 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.N1C=CC=CC=1.N1([CH:30]=[CH:31][C:32]([O:34][CH3:35])=[O:33])CCCC1>C(Cl)(Cl)Cl.Cl.O.C(N(CC)CC)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 67184N-bromobutanimideHCID 68017N-[(4-fluorophenyl)methylidene]hydroxylamineHCID 260134HCID 260134, compound

Product 1

HCID 870083HCID 870083, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.05 g of 4-fluorobenzaldoxime (Beil. 7, I 132d, II 177d, III 863c) in 15 mL of chloroform were added 1.35 g of N-bromosuccinimide (NBS) and 0.04 mL of pyridine; the resulting mixture was stirred at r.t for 4 h under nitrogen atmosphere. After cooling at 0° C., 1.75 g of methyl β-pyrrolidinoacrylate (prepared as described in U.S. Pat. No. 4,144,047) and 1.26 mL of triethylamine were added and the suspension was stirred at r.t. for 18 h. The reaction mixture was diluted with 20 mL of 2 N hydrochloric acid, 20 mL of water; the organic layer was separated, washed again with 2 N hydrochloric acid and water, dried (sodium sulphate), and evaporated to dryness in vacuo. The crude was purified by flash chromatography (toluene-dichloromethane 1:9) to afford the title compound (47%) as an oil.

Workup

  1. stirringthe suspension was stirred at r.t. for 18 h
  2. customthe organic layer was separated
  3. washwashed again with 2 N hydrochloric acid and water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated to dryness in vacuo
  6. customThe crude was purified by flash chromatography (toluene-dichloromethane 1:9)

Sources & evidence

ORD record
ord-131e36256bd046d6bc6d8b9a16f7e555
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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