Hydrazine hydrate (1:1) → 4-(Heptyloxy)benzohydrazide

HRID 716391Notes

Reaction equation

HRID 716391 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:31][NH2:32]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:31][NH2:32])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 85154p-Heptoxybenzoic acid

Product 1

HCID 43737794-(Heptyloxy)benzohydrazideYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-(heptyloxy)benzoic acid (679 mg, 2.87 mmol) in THF (5 mL) was added 1,1′-carbonyldiimidazole (559 mg, 3.45 mmol). After stirring at room temperature for 2 h, the solution was added to a stirred mixture of hydrazine hydrate (0.729 mL, 5.75 mmol) in THF (2 mL) and stirred a further 2 h. The reaction mixture was poured onto water (20 mL) and stirred for 30 min. The resulting precipitate was collected by filtration, washed with water (2×10 mL) then acetonitrile (3 mL) to afford 0.54 g (71%) of 4-(heptyloxy)benzohydrazide as a white solid. LCMS-ESI (m/z) calculated for C14H22N2O2: 250.3 found 251.0 [M+H]+, tR=2.05 min. (Method 4).

Workup

  1. stirringstirred a further 2 h
  2. additionThe reaction mixture was poured onto water (20 mL)
  3. stirringstirred for 30 min
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water (2×10 mL)

Sources & evidence

ORD record
ord-fcff32a6c60f43b4b8d3c3ed936c83b9
Source dataset
uspto-grants-2015_11
Patent number
US09187522B2

Reaction notes

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