Hydrazinium chloride → HCID 11389644, compound

HRID 1671337Notes

Reaction equation

HRID 1671337 reaction equation
[C:1]([CH:4]([C:10]([O:12]CC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].Cl.[NH2:16][NH2:17]>CCO>[CH2:8]([O:7][C:5]([C:4]1[C:10](=[O:12])[NH:16][NH:17][C:1]=1[CH3:2])=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 1363651,3-Diethyl 2-acetylpropanedioate

Product 1

HCID 11389644HCID 11389644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl acetylmalonate (20 g, 89.0 mmol) in EtOH (180 ml) is added hydrazine mono-hydrochloride (7.54 g, 107.0 mmol, 1.2 eq.) in one portion at RT. The reaction mixture is heated at reflux for 3 h then filtered hot. The filtrate is cooled to RT and concentrated under reduced pressure. The resulting crude residue is purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/[DCM/MeOH 9:1] 95:5→1:9]) to yield the title compound as a white solid. TLC: RF=0.21 (DCM/MeOH 92.5:7.5); HPLC: AtRet=0.75; MS: m/z 171.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 1.24 (t, J 7.1, 3H), 2.30 (s, 3H), 4.15 (q, J 7.1, 2H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 h
  3. filtrationthen filtered hot
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude residue is purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2
  6. washgradient elution, DCM/[DCM/MeOH 9:1] 95:5→1:9])

Sources & evidence

ORD record
ord-41ce9246e8d94e23b0cf1d6d58578def
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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