Methane → 12b-Hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydro-isoindolo[1,2-a]isoquinol-8-one

HRID 65690Notes

Reaction equation

HRID 65690 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[CH:8]1[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:15][CH2:16][N:7]1[CH2:6]2.[OH-:22].[K+].C.C[OH:26]>CN(C)C=O>[OH:22][C:8]12[C:17]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:19]([O:20][CH3:21])[CH:18]=3)[C:6](=[O:26])[N:7]1[CH2:16][CH2:15][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12

Participants

6

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 14797Potassium HydroxideHCID 2275755610,11-Dimethoxy-5,6,8,12b-tetrahydro-isoindolo-[1,2-a]isoquinoline

Product 1

HCID 2275755212b-Hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydro-isoindolo[1,2-a]isoquinol-8-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

10,11-Dimethoxy-5,6,8,12b-tetrahydro-isoindolo-[1,2-a]isoquinoline (109.65 g) and potassium hydroxide in pellet form (23.2 g) are dissolved in methanol (1100 cc). Air is bubbled into the reaction mixture, which is heated under reflux for 3 hours and then maintained at 25° C. for 48 hours. After concentration to 500 cc, the addition of distilled water (5000 cc) and stirring for 2 hours, a precipitate appears which is filtered off, washed three times with distilled water (total 500 cc) and dried under reduced pressure (20 mm Hg) at 40° C. A crude product (104.65 g), melting at 219° C., is obtained. A solution of a portion of this product (30 g) in dimethylformamide (200 cc) at 120° C. is treated with decolourising charcoal (1 g), filtered whilst hot, and cooled at about 5° C. for 16 hours. The resulting crystals are filtered off, washed three times with diisopropyl ether (total 30 cc) and dried under reduced pressure (1 mm Hg) at 60° C. for 6 hours. 12b-Hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydro-isoindolo[1,2-a]isoquinol-8-one (16.70 g), melting at 220° C., is thus obtained.

Workup

  1. customAir is bubbled into the reaction mixture, which
  2. temperatureis heated
  3. temperatureunder reflux for 3 hours
  4. concentrationAfter concentration to 500 cc
  5. additionthe addition of distilled water (5000 cc)
  6. filtrationis filtered off
  7. washwashed three times with distilled water (total 500 cc)
  8. customdried under reduced pressure (20 mm Hg) at 40° C
  9. customA crude product (104.65 g), melting at 219° C., is obtained
  10. filtrationfiltered whilst hot, and
  11. temperaturecooled at about 5° C. for 16 hours
  12. filtrationThe resulting crystals are filtered off
  13. washwashed three times with diisopropyl ether (total 30 cc)
  14. customdried under reduced pressure (1 mm Hg) at 60° C. for 6 hours

Sources & evidence

ORD record
ord-a4e9fc9807d647e085e712d43f19459d
Source dataset
uspto-grants-1978_12
Patent number
US04128650

Reaction notes

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