Hydrazinium chloride → HCID 18705826, compound

HRID 2287883Notes

Reaction equation

HRID 2287883 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:17]([O-])=[O:18])=[C:10]([C:14]([O-])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].Cl.[NH2:24][NH2:25]>CC(O)=O>[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2=[CH:11][C:10]3[C:14](=[O:15])[NH:24][NH:25][C:17](=[O:18])[C:9]=3[CH:8]=[C:7]2[CH2:6]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 18705881HCID 18705881, compound

Product 1

HCID 18705826HCID 18705826, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-(dipropylamino)-2,3-dihydro-1H-indene-5,6-dicarboxylate (92, 0.17 g, 0.5 mmol) and hydrazine hydrochloride (0.05 g, 0.7 mmol) in glacial HOAc (10 mL) was refluxed at 125° C. for 4 h. The reaction was cooled, concentrated, and converted to an HCl salt. The resulting solid was recrystallized from EtOAc/MeOH to give a white solid. This white solid was further purified via reverse phase chromatography eluting with H2O/MeOH (95:5). The resulting product was converted to an HCl salt and recrystallized from hot MeOH to give 134 as a white solid (m.p.>300° C.).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customThe resulting solid was recrystallized from EtOAc/MeOH
  4. customto give a white solid
  5. customThis white solid was further purified via reverse phase chromatography
  6. washeluting with H2O/MeOH (95:5)
  7. customrecrystallized from hot MeOH

Sources & evidence

ORD record
ord-f55400c31b0942f4af287540d4a1f656
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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