Hydrochloric Acid → HCID 68131886, compound

HRID 1729711Notes

Reaction equation

HRID 1729711 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:19]3[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([CH2:15][CH2:16][CH2:17][CH2:18]3)[N:13](O)[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[ClH:27]>[Zn].CO>[ClH:27].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:19]3[C:14]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([CH2:15][CH2:16][CH2:17][CH2:18]3)[NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21500388HCID 21500388, compound

Product 1

HCID 68131886HCID 68131886, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Zinc powder (20 g) was added to a stirred solution of 6.5 g (0.018 mole) of 3-(3,4-dimethoxyphenyl)-hexahydro-1-hydroxy-7a-phenylindoline, 150 ml of methanol and 150 ml of 1N hydrochloric acid and the mixture was maintained at reflux for 1/2 hour. The mixture was cooled, treated with excess of 10MKOH and extracted with two one liter portions of ether. The extracts were combined, dried (K2CO3) and filtered. Hydrogen chloride gas was bubbled into the ether solution until complete precipitation of the white salt; wt. 4.5 g (67.2%), mp 303°-305° C. Recrystallization from methanol-ether afforded pure white crystals, mp 303°-305° C.

Workup

  1. temperaturethe mixture was maintained
  2. temperatureat reflux for 1/2 hour
  3. temperatureThe mixture was cooled
  4. additiontreated with excess of 10MKOH and
  5. extractionextracted with two one liter portions of ether
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. customHydrogen chloride gas was bubbled into the ether solution until complete precipitation of the white salt
  9. customRecrystallization from methanol-ether afforded pure white crystals, mp 303°-305° C.

Sources & evidence

ORD record
ord-0f12b932248141b3a688cb956f34e98f
Source dataset
uspto-grants-1976_11
Patent number
US03989714

Reaction notes

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