Hydrochloric Acid → HCID 18705864, compound

HRID 2287878Notes

Reaction equation

HRID 2287878 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[CH:5]1[CH2:24][C:8]2=[CH:9][C:10]3[C:11](=[O:23])[N:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13](=O)[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:2][CH3:3].Cl>CC(O)=O.[Zn]>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:24][C:8]2=[CH:9][C:10]3[C:11](=[O:23])[N:12]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:13][C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18705859HCID 18705859, compound

Product 1

HCID 18705864HCID 18705864, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Using procedure 47, 6-(dipropylamino)-6,7-dihydro-2-phenylcyclopent[f]isoindole-1,3(2H,5H)-dione (121, 0.09 g, 0.23 mmol) was reduced with Zinc dust (0.15 g, 2.3 mmol) in glacial HOAc (5 mL). Purification on silica gel, eluting with 3:1 hexane/acetone gave an oil that was converted to an HCl salt and recrystallized from EtOAc/MeOH to give 127 as a white solid (m.p. 248-249° C.).

Workup

  1. customPurification on silica gel
  2. washeluting with 3:1 hexane/acetone
  3. customgave an oil that
  4. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-bea2f8c9c9ed4067a18dc46af17544ed
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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