Hydrochloric Acid → HCID 21500384, compound

HRID 1729708Notes

Reaction equation

HRID 1729708 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:19]3[CH:14]([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:21]>[Zn]>[ClH:21].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:19]3[CH:14]([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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21500383HCID 21500383, compound

Product 1

HCID 21500384HCID 21500384, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 10.0 g (0.036 mole) of 3-(3,4-dimethoxyphenyl)hexahydro-1-hydroxyindoline base, 400 ml of 1N hydrochloride acid (0.4 mole) and 20 g of zinc dust was heated with stirring on the steam bath for 11/2 hours. The cooled mixture was decanted (still acid to congo red) and 10M KOH (150 ml) was added. The separated oil was ether extracted (800 ml) and the ether solution was dried (K2CO3), filtered and treated with HCl gas to precipitate solid salt; wt. 9.5 g (84.2%), mp 188°-198° C. Recrystallization from 2-propanol-ether gave pure material melting at 190°-192° C.

Workup

  1. temperaturewas heated
  2. customThe cooled mixture was decanted (still acid to congo red) and 10M KOH (150 ml)
  3. additionwas added
  4. extractionextracted (800 ml)
  5. dry with materialthe ether solution was dried (K2CO3)
  6. filtrationfiltered
  7. additiontreated with HCl gas
  8. customto precipitate solid salt
  9. customRecrystallization from 2-propanol-ether

Sources & evidence

ORD record
ord-0bb69faf547a430087b221b0baf2d006
Source dataset
uspto-grants-1976_11
Patent number
US03989714

Reaction notes

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