Hydrazine hydrate (1:1) → 7-[2-Hydroxy-5-(3-hydroxy-1-octenyl)-cyclopentyl]heptanohydrazide

HRID 1581116Notes

Reaction equation

HRID 1581116 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=O.O.[NH2:27][NH2:28]>CO>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:27][NH2:28])=[O:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

Product 1

HCID 540860897-[2-Hydroxy-5-(3-hydroxy-1-octenyl)-cyclopentyl]heptanohydrazideYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (0.4 g.), [prepared as described in Example 5], 100% hydrazine hydrate (0.8 ml.) and methanol (10 ml.) was refluxed for 24 hours. After 12 hours reflux a further amount of hydrazine hydrate (0.8 ml.) was added. The methanol was removed in vacuo and the residue diluted with water. The resulting solution was extracted twice with diethyl ether. The combined ether extracts were dried over magnesium sulphate to give 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)-cyclopentyl]heptanohydrazide (0.25 g., 62.5%). (Found: C, 67.4; H, 10.6; N, 7.9. C20H38N2O3 requires C, 67.8; H,10.72; N, 7.9%) νmax 3300 cm-1, 1650 cm-1 (shoulder 1630 cm-1), 980 cm-1 (liquid film).

Workup

  1. additionwas added
  2. customThe methanol was removed in vacuo
  3. additionthe residue diluted with water
  4. extractionThe resulting solution was extracted twice with diethyl ether
  5. dry with materialThe combined ether extracts were dried over magnesium sulphate

Sources & evidence

ORD record
ord-9428c17389b746b196170b4c30d98f09
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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