Hydrochloric Acid → HCID 178515418, compound

HRID 1707034Notes

Reaction equation

HRID 1707034 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]([C:11](=[CH:17][NH:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10].Cl>O.O1CCCC1>[NH:5]1[C:9]([C:11]2[C:12](=[O:13])[N:20]3[CH:21]=[CH:22][C:23]4[CH2:24][CH2:25][CH2:26][CH2:27][C:28]=4[C:19]3=[N:18][CH:17]=2)=[N:10][N:7]=[N:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 70583309Ethyl 2-Cyano-3-(5,6,7,8-tetrahydro-1-isoquinolylamino)-acrylate

Product 1

HCID 178515418HCID 178515418, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (2.05 g., 0.0154 mole) was added to cold (-30° C.) tetrahydrofuran (75 ml.). Sodium azide was added and the mixture heated under reflux for 40 minutes. Ethyl 2-cyano-3-(5,6,7,8-tetrahydro-1-isoquinolylamino)-acrylate (3.33 g., 0.0123 mole) was added and the mixture heated under reflux for 20 hours. The cooled mixture was diluted with water (100 ml.) and acidified with concentrated hydrochloric acid. The precipitate was collected, washed with water, dried and recrystallized from 2-methoxyethanol to give the title compound (0.625 g., 19%), m.p. 290°-292° C. (decomp.).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 40 minutes
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 20 hours
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried
  8. customrecrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-9b70d8fc53ab47ddb5fffd815045b648
Source dataset
uspto-grants-1980_06
Patent number
US04209620

Reaction notes

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