HCID 20063315, compound → HCID 20063351, compound

HRID 1084431Notes

Reaction equation

HRID 1084431 reaction equation
[OH:1][CH:2]([CH2:7][CH:8]([OH:29])/[CH:9]=[CH:10]/[C:11]1[N:12]([CH3:28])[C:13](=[O:27])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3][C:4](O)=[O:5]>C1(C)C=CC=CC=1.C(O)(=O)C>[OH:1][CH:2]1[CH2:7][CH:8](/[CH:9]=[CH:10]/[C:11]2[N:12]([CH3:28])[C:13](=[O:27])[C:14]3[C:19]([C:20]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:29][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 1

HCID 20063315HCID 20063315, compound

Product 1

HCID 20063351HCID 20063351, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalyst2×HCID 1140TolueneSolvent2×

Procedure

A stirred mixture of a 2:1 mixture of the erythro- and threo-diastereoisomers of (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoic acid (0.1 g; prepared as described in Example 2) in dry toluene (10 ml) and glacial acetic acid (2 drops) was heated at reflux for 1 hour. Further quantities of toluene (15 ml) and glacial acetic acid (2 drops) were added and the mixture was heated at reflux for a further period of 3.5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to half volume. The resulting white solid was filtered off and washed with petroleum ether (b.p. 40°-60° C.), to give (E)-4-hydroxy-6-[2-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethenyl]-3,4,5,6-tetrahydro-2H-pyran-2-one (0.07 g), m.p. 190°-193° C. [Elemental analysis: C, 71.1; H, 5.52; N, 3.52%; calculated for C23H21NO4 : 0.75 H2O: C, 71.0; H, 5.8; N, 3.6%].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe mixture was heated
  4. temperatureat reflux for a further period of 3.5 hours
  5. concentrationconcentrated under reduced pressure to half volume
  6. filtrationThe resulting white solid was filtered off
  7. washwashed with petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-0fc8b213a9de43dda7bdbab1cd16684e
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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