Hydrochloric Acid → HCID 18705846, compound

HRID 2287880Notes

Reaction equation

HRID 2287880 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17](=O)[C:16]3[CH:15]=[C:14]4[CH2:19][CH:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:21][C:13]4=[CH:12][C:11]=3[C:10]2=[O:29])=[CH:4][CH:3]=1.Cl>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:10](=[O:29])[C:11]3[CH:12]=[C:13]4[CH2:21][CH:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:19][C:14]4=[CH:15][C:16]=3[CH2:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18705827HCID 18705827, compound

Product 1

HCID 18705846HCID 18705846, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Using procedure 47, 2-[(4-Chlorophenyl)methyl]-6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione (102, 0.59 g, 1.43 mmol) was reduced with Zinc dust (0.94 g, 14.3 mmol) in glacial HOAc (100 mL). Purification using silica gel, eluting with 4:1 hexane/acetone, afforded an oil that was converted to an HCl salt and recrystallized from EtOAc/MeOH to give 129 as a white solid (m.p. 233-234° C.).

Workup

  1. customPurification
  2. washeluting with 4:1 hexane/acetone
  3. customafforded an oil that
  4. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-272499fe351447f69dfe67a1403361ec
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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