Hydrochloric Acid → 1-Hydrazinyl-3,4-dihydroisoquinoline

HRID 436430

Reaction equation

HRID 436430 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.Cl.C(OC1C2C(=CC=CC=2)CC[N:17]=1)C.[Cl-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+].NN>C(O)C>[NH:1]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1)[NH2:17]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 97938243,4-Dihydro-isoquinolin-1-ylamineHCID 123490381-Ethoxy-3,4-dihydroisoquinoline

Product 1

HCID 123490411-Hydrazinyl-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-amino-3,4-dihydroisoquinoline (VI: R=R'=Y=Y'=Z=Z'=H) hydrochloride (m.p. 133°-134° C., 0.5 g.), prepared from 1-ethoxy-3,4-dihydroisoquinoline and ammonium chloride, sodium carbonate (0.38 g.), hydrazine (0.41 g.) and ethanol (15 ml.) was stirred (at 25° C.). The mixture was filtered. An ether solution of the crystals which separated from the filtrate on chilling was washed with water, dried and filtered. Concentration of the filtrate and crystallization of the residue from ether afforded 1-hydrazino-3,4-dihydroisoquinoline (0.44 g.).

Workup

  1. filtrationThe mixture was filtered
  2. customAn ether solution of the crystals which separated from the filtrate
  3. temperatureon chilling
  4. washwas washed with water
  5. customdried
  6. filtrationfiltered
  7. customConcentration of the filtrate and crystallization of the residue from ether

Sources & evidence

ORD record
ord-c56f3b2b50184e3084ea8ec85fc05f53
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Linked notes

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