HCID 18931278, compound → HCID 18931134, compound

HRID 1598992Notes

Reaction equation

HRID 1598992 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([O:17][CH3:18])=[CH:10][C:9]=1[O:19][CH3:20])=[O:7]>[Pd].C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([O:17][CH3:18])=[CH:10][C:9]=1[O:19][CH3:20])=[O:7]

Participants

4

Reactant 1

HCID 18931278HCID 18931278, compound

Product 1

HCID 18931134HCID 18931134, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-1-(2,4-dimethoxy-5-nitrophenyl)-1-pentanone (2.9 g, 9.6 mmol), prepared as in Example 12, 10% palladium on carbon (650 mg) and THF (approximately 170 mL) was stirred 3 hours under a hydrogen atmosphere (15 psi). The mixture was filtered and concentrated and the residue was purified by column chromatography eluting with hexane/ethyl acetate (60:40) to give 5-chloro-1-(5-amino-2,4-dimethoxyphenyl)-1-pentanone (1.9 g, 7 mmol), m.p. 87°-88° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography
  4. washeluting with hexane/ethyl acetate (60:40)

Sources & evidence

ORD record
ord-fafeff2a610149b782ac93769398788c
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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