Methanol → HCID 13046464, compound

HRID 1105737Notes

Reaction equation

HRID 1105737 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-cb7a8dfcb3774dc9a3c2a521b78b1972
Source dataset
uspto-grants-1982_01
Patent number
US04309545

Reaction notes

Loading…