Acetonitrile → HCID 20081991, compound

HRID 1609492Notes

Reaction equation

HRID 1609492 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH:9]=CN)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]1(=[O:25])[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[CH2:15]1.[C:26](#[N:28])C>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:15]([C:14]([OH:20])=[O:25])[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18](=[O:19])[N:28]2[CH3:26])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 12801Homophthalic anhydrideHCID 67690086HCID 67690086, compound

Product 1

HCID 20081991HCID 20081991, compound

Procedure

To 170 ml of a solution containing 18.67 g of N-(4-t-butylbenzylidene)methylamine in acetonitrile, 18.00 g of homophthalic anhydride was added and the mixture was allowed to react at room temperature for 14 hours. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography [chloroform/ethyl acetate (6/1)] to obtain 33.73 g of 3-(4-t-butylphenyl)-4-hydroxycarbonyl-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline (mixture of diastereomers). The thus obtained mixture of diastereomers was again subjected to silica gel column chromatography [chloroform/ethyl acetate (6/1)] to obtain 15.2 g of cis compound and 8.03 g of trans compound.

Workup

  1. additionwas added
  2. customto react at room temperature for 14 hours
  3. customAfter evaporating the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [chloroform/ethyl acetate (6/1)]

Sources & evidence

ORD record
ord-d6ffdfd6d851483aadc82278b2e9938e
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

Loading…