Sodium → HCID 10431342, compound

HRID 2396510Notes

Reaction equation

HRID 2396510 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=[C:12]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Na]>C(O)C.O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=[C:12]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 10478045HCID 10478045, compound

Product 1

HCID 10431342HCID 10431342, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The yellow suspension obtained by mixing ethyl 6-{[4-(4-nitrophenyl)-6-phenyl-2-pyridyl]oxy}hexanoate (5.3 g), stannous chloride (11.6 g) in ethanol (100 cc) is heated at 70° C. for 2 hours and 30 minutes under inert atmosphere. The clear brown solution thus obtained is concentrated to dryness under reduced pressure. The residue obtained is taken up in distilled water (100 cc). The pH of this aqueous phase is brought to 6 by addition of sodium hydrogenocarbonate. The solution is then extracted with ethyl acetate (3×200 cc). The organic phases are combined, washed with distilled water (3×50 cc), dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The residue obtained is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 7-3). (yellowish oil).

Workup

  1. customThe yellow suspension obtained
  2. customThe clear brown solution thus obtained
  3. concentrationis concentrated to dryness under reduced pressure
  4. customThe residue obtained
  5. extractionThe solution is then extracted with ethyl acetate (3×200 cc)
  6. washwashed with distilled water (3×50 cc)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated to dryness at 40° C. under reduced pressure
  9. customThe residue obtained
  10. customis purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 7-3)

Sources & evidence

ORD record
ord-901d0f62bcfa47cf84897f95e70aa165
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

Loading…