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

HRID 457360Notes

Reaction equation

HRID 457360 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. Flash 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. customFlash column chromatography of the residue (silica gel, 2:1 hexane, EtOAc) provides a creamy solid

Sources & evidence

ORD record
ord-959b42f574f145bea968b3d998b7387c
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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