Acetic Anhydride → HCID 57324321, compound

HRID 1290977Notes

Reaction equation

HRID 1290977 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]2[CH2:19][CH2:18][C:17]3[N+:16]([O-])=[CH:15][C:14]([CH3:21])=[CH:13][C:12]=3[CH2:11]2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:24])C>C1(C)C=CC=CC=1>[OH:24][C@@H:18]1[C:17]2[N:16]=[CH:15][C:14]([CH3:21])=[CH:13][C:12]=2[CH2:11][C@H:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18659969HCID 18659969, compound

Product 1

HCID 57324321HCID 57324321, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(+)-(6S)-5,6,7,8-Tetrahydro-6-((4-methoxyphenyl)methyl)-3-methylquinoline-N-oxide (3,48g 0.012 mol) in toluene (40 ml) was added slowly to refluxing acetic anhydride (18 ml) and the mixture stirred for a further 3 hours. After cooling overnight, the reaction mixture was concentrated under reduced pressure and dissolved in methanol. The resulting solution was treated with 5M KOH until it was basic and again concentrated under reduced pressure. The residue was dissolved in water (40 ml) and washed with chloroform (3×40 ml). The combined organic phases were washed with brine (1×40 rml), dried (MgSO4) and concentrated under reduced pressure to give an oil (3.98 g) which solidified on standing. The product (1.9 g) was chromatographed on silica gel eluting with ethyl acetate to give the title compound (0.21 g), [α]D25 =+115% (1% CHCl3) mp 105°-7° C.

Workup

  1. temperatureAfter cooling overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in methanol
  4. additionThe resulting solution was treated with 5M KOH until it
  5. concentrationagain concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in water (40 ml)
  7. washwashed with chloroform (3×40 ml)
  8. washThe combined organic phases were washed with brine (1×40 rml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5517699a4091445b9be8028686999af2
Source dataset
uspto-grants-1998_05
Patent number
US05753676

Reaction notes

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