Hydrochloric Acid → HCID 18705825, compound

HRID 2287851Notes

Reaction equation

HRID 2287851 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[NH:12][C:13](=[O:16])[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:2][CH3:3].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1.Cl>>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[N:12]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=4)[C:13](=[O:16])[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 869964-(Bromomethyl)benzonitrileHCID 18705862HCID 18705862, compound

Product 1

HCID 18705825HCID 18705825, compound

Procedure

Using procedure 48, 6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione (93, 0.12 g, 0.4 mmol) was treated with alpha-bromo-p-tolunitrile (0.08 mL, 0.4 mmol). Purification using silica gel, eluting with 3:1 hexane/acetone, afforded a solid that was converted to an HCl salt and recrystallized from hot MeOH/EtOAc to give 97 as a white solid (m.p. 263-264° C.).

Workup

  1. customPurification
  2. washeluting with 3:1 hexane/acetone
  3. customafforded a solid
  4. customrecrystallized from hot MeOH/EtOAc

Sources & evidence

ORD record
ord-8f6a54c734db4e93958ce3d834dd8d0a
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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