Methanol → HCID 13046464, compound

HRID 1703339Notes

Reaction equation

HRID 1703339 reaction equation
CO[C:3]1C=C(CNCCCNCCCCNCCCN)[CH:6]=[CH:5][C:4]=1[OH:24].O[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:38])[CH:34]=2)[C:29](=[O:44])[C:28](=[CH:45][OH:46])[CH:27]1[CH3:47].C([C:50](C)=[O:51])=C.C(N(CC)CC)C.C[OH:61]>CCOCC.C1C=CC=CC=1>[CH:50]([N:26]1[C:35]2[C:30](=[C:31]([OH:61])[CH:32]=[C:33]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:38])[CH:34]=2)[C:29](=[O:44])[C:28]([CH:45]=[O:46])([CH2:6][CH2:5][C:4](=[O:24])[CH3:3])[CH:27]1[CH3:47])=[O:51]

Participants

7

Reactant 4

HCID 887MethanolHCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 131712638HCID 131712638, compound

Product 1

HCID 13046464HCID 13046464, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of dl-5-hydroxy-3-hydroxymethylene-2-methyl-7-(2-heptyloxy)-4-oxo-1,2,3,4-tetrahydroquinoline (13.1 g., 37.7 mmol.), in methanol (56 ml.) and methyl vinyl ketone (5.52 mg., 68 mmol.) is added triethylamine (1.3 ml., 9.3 mmol.). The mixture is stirred for 18 hours under a nitrogen atmosphere at room temperature and is then diluted with ether (550 ml.). The solution is washed with 10% aqueous sodium bicarbonate solution (4×60 ml.), followed by brine (1×100 ml.) and dried (MgSO4). Removal of the ether by evaporation gives a dark oil (16 g.). The oil is dissolved in a minimum volume of benzene and the solution charged to a column of silica gel (500 g.). The column is then eluted with a volume of benzene equal to the volume of the column. The eluting solvent is then changed to 15% ether-benzene and 100 ml. fractions collected when the first color band begins to elute off the column. Fractions 5- 13 are combined and concentrated under reduced pressure to give dl-1,3-diformyl-5-hydroxy-2-methyl-7-(2-heptyloxy)-4-oxo-3-(3-oxobutyl)-1,2,3,4-tetrahydroquinoline as a yellow oil (8.7 g.).

Workup

  1. washThe solution is washed with 10% aqueous sodium bicarbonate solution (4×60 ml.)
  2. dry with materialdried (MgSO4)
  3. customRemoval of the ether
  4. customby evaporation
  5. customgives a dark oil (16 g.)
  6. additionthe solution charged to a column of silica gel (500 g.)
  7. washThe column is then eluted with a volume of benzene equal to the volume of the column
  8. customfractions collected when the first color band
  9. washto elute off the column
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f993ffe0c40e4803801c38ee9f648318
Source dataset
uspto-grants-1982_09
Patent number
US04351833

Reaction notes

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