Hydrazine hydrate (1:1) → HCID 178439697, compound

HRID 729008Notes

Reaction equation

HRID 729008 reaction equation
C[N:2](C)/[CH:3]=[CH:4]\[C:5]([C:7]1[CH:33]=[CH:32][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:28]=[CH:27][C:19]3[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=3[C:17]=2[CH2:29][CH2:30][CH3:31])=[C:9]([CH2:34][CH2:35][CH3:36])[C:8]=1[O:37][CH3:38])=O.O.[NH2:41]N.Cl.C(OCC)(=O)C>CO>[CH3:38][O:37][C:8]1[C:9]([CH2:34][CH2:35][CH3:36])=[C:10]([CH:32]=[CH:33][C:7]=1[C:5]1[CH:4]=[CH:3][NH:2][N:41]=1)[O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:28]=[CH:27][C:19]2[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=2[C:17]=1[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 14989449HCID 14989449, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 178439697HCID 178439697, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude compound from Example 5 was stirred in 4.0 ml of methanol/1.0 ml water with 0.1 ml hydrazine hydrate at reflux for 2.0 hours. The reaction mixture was poured into 1N hydrochloric acid/ethyl acetate, and the ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated under vacuum. Flash chromatography of the concentrate on silica gel using 5:1 to 2:1 hexane/ethyl acetate (1% acetic acid) as eluant gave the product, melting point 156°-158° C.

Workup

  1. temperatureat reflux for 2.0 hours
  2. washthe ethyl acetate layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. concentrationFlash chromatography of the concentrate on silica gel using 5:1 to 2:1 hexane/ethyl acetate (1% acetic acid) as eluant
  6. customgave the product, melting point 156°-158° C.

Sources & evidence

ORD record
ord-9cdc63acb4374915991c6baa591f2b4f
Source dataset
uspto-grants-1991_09
Patent number
US05051438

Reaction notes

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