Pyridine → HCID 18403464, compound

HRID 1017210Notes

Reaction equation

HRID 1017210 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22]>C(Cl)Cl.Cl>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][NH:11][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 122944662-(4-nitrophenoxy)ethanamine

Product 1

HCID 18403464HCID 18403464, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-(4-Nitro-phenoxy)ethylamine (0.27 g) was dissolved in dry DCM (8.5 ml) and dry pyridine (0.15 ml) and isobutyryl chloride (0.12 ml) were then added. After stirring for 1 h at room temperature, the reaction mixture was then diluted with HCl 3 N (50 ml) and extracted with ethyl acetate (50 ml), then the organic phase was washed with brine (50 ml). The organic layer was separated, dried, filtered and evaporated under vacuum to give a crude product which was crystallized (diethyl ether, 7 ml) to give the title compound (0.11 g) as a yellow solid. m.p. 102-103°.

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washthe organic phase was washed with brine (50 ml)
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give a crude product which
  8. customwas crystallized (diethyl ether, 7 ml)

Sources & evidence

ORD record
ord-a3979d4e05dc4badb73fa6fce8d45f95
Source dataset
uspto-grants-2002_11
Patent number
US06479488B1

Reaction notes

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