Hydrazine hydrate (1:1) → HCID 19605262, compound

HRID 1603636Notes

Reaction equation

HRID 1603636 reaction equation
C1(=O)[N:5]([C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)C(=O)C2=CC=CC=C12.[H][H].O.NN>CO.CCOCC.[Pt]=O>[Cl:18][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH2:5])[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 19605323HCID 19605323, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19605262HCID 19605262, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of 1-(phthalimido)-6-(3-chlorophenyl)hex-1-yne (10 g, 30 mmol) in methanol (100 ml) was treated with platinum oxide (250 mg) and the mixture hydrogenated at 50 psi for 72 h. Further quantities of catalyst were added at intervals and when the theoretical uptake of hydrogen was complete, the mixture was filtered and the filtrate evaporated to a brown oil (9.5 g, 96%). This was dissolved in IMS 99 (100 ml) and treated with hydrazine hydrate (2.8 g, 56 mmol) under reflux for 16 h. The mixture was cooled to 5° C. and the precipitated solid removed by filtration. Evaporation of the filtrate gave an oil which was taken up in ether, washed with water, dried (Na2SO4) and evaporated to a brown oil (5.8 g, 98%)

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated to a brown oil (9.5 g, 96%)
  3. dissolutionThis was dissolved in IMS 99 (100 ml)
  4. temperatureunder reflux for 16 h
  5. customthe precipitated solid removed by filtration
  6. customEvaporation of the filtrate
  7. customgave an oil which
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated to a brown oil (5.8 g, 98%)

Sources & evidence

ORD record
ord-df96d5150dc8417a8f3dd3776bee2686
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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