Hydrochloric Acid → 3,4-Dimethoxy-N-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzene-1-carboximidic acid--hydrogen chloride (1/1)

HRID 2397928Notes

Reaction equation

HRID 2397928 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[CH:14]2)=[O:7].CO.[ClH:26]>[Pt]=O>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH2:14]2)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21436744HCID 21436744, compound

Product 1

HCID 2165813,4-Dimethoxy-N-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzene-1-carboximidic acid--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

5-(3,4-dimethoxybenzamido) isoquinoline (2.7 g) was dissolved in 10% hydrochloric acid (100 ml) and methanol (100 ml) with warming. This was hydrogenated over platinum oxide (200 mg) at 45 psi. The catalyst was removed by filtration and the filtrate cooled in the refrigerator. A white precipitate formed and was collected by filtration and recrystallized from methanol to yield 2.1 g of 5-(3,4-dimethoxybenzamido)-1,2,3,4-tetrahydroisoquinoline hydrochloride as a white crystalline powder, m.p., 287°-288° C.

Workup

  1. customThe catalyst was removed by filtration
  2. temperaturethe filtrate cooled in the refrigerator
  3. customA white precipitate formed
  4. filtrationwas collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0992f9f7954840ccb9e0c2da0d615df8
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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