Hydrazine hydrate (1:1) → HCID 18438122, compound

HRID 1643194Notes

Reaction equation

HRID 1643194 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8][CH3:9].O.[NH2:20][NH2:21]>C(O)C>[CH2:6]([CH:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:21][NH:20][C:3](=[O:2])[CH2:4]1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66756925HCID 66756925, compound

Product 1

HCID 18438122HCID 18438122, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-benzoyl-heptanoic acid methyl ester (4.72 g, 19 mmol) and hydrazine monohydrate (4.6 ml, 95 mmol) in ethanol (50 mL) is reflux for 12 hours. The solvent and excess hydrazine monohydrate is removed in vacuo and the residue is partitioned with EtOAc (80 mL) and water (80 mL). The layers are separated and the organic phase is washed with brine (60 mL), dried (Na2SO4) and evaporated in vacuo. Hash column chromatography of the residue (silica gel, 2:1 hexane, EtOAc) provides a creamy solid. LC-MS (M+1) 231. 1H NMR (δ, CDCl3) 8.84 (s, 1H), 7.72-7.79 (m, 2H), 7.37-7.43 (m, 3H), 3.19-3.30 (m, 1H), 2.62 (d, J=6.8 Hz, 2H), 1.52-1.62 (m, 2H), 1.21-1.43 (m, 4H), 0.87 (t, J=7.8 Hz, 3H).

Workup

  1. customThe solvent and excess hydrazine monohydrate is removed in vacuo
  2. customthe residue is partitioned with EtOAc (80 mL) and water (80 mL)
  3. customThe layers are separated
  4. washthe organic phase is washed with brine (60 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customHash column chromatography of the residue (silica gel, 2:1 hexane, EtOAc) provides a creamy solid

Sources & evidence

ORD record
ord-fad8687563934cf0a475bed227ba09c9
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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