Trifluoroacetic acid → 5-Chloro-2-hydroxy-6-[3-methoxypyrrolidin-1-yl]-benzo[de]isoquinoline-1,3-dione

HRID 279028Notes

Reaction equation

HRID 279028 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][N:13]1[C:22](=[O:23])[C:21]2[CH:24]=[C:25]([Cl:34])[C:26]([N:27]3[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28]3)=[C:19]3[C:20]=2[C:15](=[CH:16][CH:17]=[CH:18]3)[C:14]1=[O:35])(C)(C)C>>[Cl:34][C:25]1[C:26]([N:27]2[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28]2)=[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:20]2=[C:21]([CH:24]=1)[C:22](=[O:23])[N:13]([OH:12])[C:14]3=[O:35]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226239382-tert-Butyloxy-5-chloro-6-[3-methoxypyrrolidin-1-yl]-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226240545-Chloro-2-hydroxy-6-[3-methoxypyrrolidin-1-yl]-benzo[de]isoquinoline-1,3-dione

Procedure

Following the procedure from Example 62, TFA (1.0 mL) and 2-tert-butyloxy-5-chloro-6-[3-methoxypyrrolidin-1-yl]-benzo[de]isoquinoline-1,3-dione (0.2 g, 0.5 mmol, from Example S2) was stirred at room temperature overnight, concentrated, and the solid recrystallized from ethanol/ether solution to give 0.02 of the title compound, mp 136-142° C.

Workup

  1. concentrationconcentrated
  2. customthe solid recrystallized from ethanol/ether solution

Sources & evidence

ORD record
ord-d6560332277e4efbac650d484b948bc1
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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