Hydrazine hydrate (1:1) → HCID 11075364, compound

HRID 1856782Notes

Reaction equation

HRID 1856782 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3C(=O)C4=CC=CC=C4C3=O)[CH2:10]2)=[CH:5][CH:4]=1.O.NN>C(O)C>[NH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 221325287-Methoxy-2-(4-phthalimidobutyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 11075364HCID 11075364, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-methoxy-2-(4-phthalimidobutyl)-1,2,3,4-tetrahydroisoquinoline (17.4 g 0.0478 mol) and hydrazine monohydrate (4.6 ml, 0.095 mol) in ethanol (300 ml) were stirred at room temperature for 18 h and at reflux for 1 h. The cooled reaction mixture was filtered and the filtrate evaporated in vacuo. The residue was dissolved in 2.5N hydrochloric acid, filtered through Kieselguhr and the filtrate basified with 0.880 ammonia. The product was extracted into dichloromethane (4×200 ml), the combined extracts were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil (7 g, 63%).

Workup

  1. temperatureat reflux for 1 h
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue was dissolved in 2.5N hydrochloric acid
  6. filtrationfiltered through Kieselguhr
  7. extractionThe product was extracted into dichloromethane (4×200 ml)
  8. dry with materialthe combined extracts were dried (Na2SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c81f12c43441423a8620df60af7ae20b
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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