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

HRID 1603669Notes

Reaction equation

HRID 1603669 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.[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

6

Reactant 3

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

Product 1

HCID 19605262HCID 19605262, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

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 ethanol (100 ml) and treated with hydrazine hydrate (2.8 g, 56 mmol) under reflux for 16 h. The mixture was cooled to 5°

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated to a brown oil (9.5 g, 96%)
  3. dissolutionThis was dissolved in ethanol (100 ml)
  4. temperatureunder reflux for 16 h
  5. temperatureThe mixture was cooled to 5°

Sources & evidence

ORD record
ord-d877e2fbbf824a8ea1eb6d0567a638c3
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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