Hydrochloric Acid → HCID 10250881, compound

HRID 2380338Notes

Reaction equation

HRID 2380338 reaction equation
[CH3:1][C:2]([CH3:31])([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)[C:3]([O:5]C)=[O:4].[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C>[CH3:1][C:2]([CH3:31])([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 10025248HCID 10025248, compound

Product 1

HCID 10250881HCID 10250881, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

The mixture comprising methyl 2,2-dimethyl-6-{[4-(4-nitrophenyl)-2-quinolyl]oxy}hexanoate (2.95 g) and dry lithium iodide (6.1 g) in 2,4,6-collidine (115 cc) is refluxed, under inert atmosphere, for 1 hour and 30 minutes and then poured in a 2N solution of hydrochloric acid (150 cc) at 0° C. The aqueous phase is extracted with ethyl ether (3×50 cc). The combined organic phases are washed with distilled water until neutrality, dried over sodium sulphate and then concentrated to dryness under reduced pressure. The residue obtained is purified by chromatography on silica gel (30-60 mm; n-hexane-ethyl acetate 1--1, white solid; m.p.=85°-92° C.)

Workup

  1. extractionThe aqueous phase is extracted with ethyl ether (3×50 cc)
  2. washThe combined organic phases are washed with distilled water until neutrality
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel (30-60 mm; n-hexane-ethyl acetate 1--1, white solid; m.p.=85°-92° C.)

Sources & evidence

ORD record
ord-88ba49ad83294952ac88a1b7c154e559
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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