Methanol--water (1/1) → 5-Bromo-2-hydroxy-6-(3-methylpiperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 279015Notes

Reaction equation

HRID 279015 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:30])[C:22]([N:23]3[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:31])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3].O.CO>C(O)(C(F)(F)F)=O>[Br:30][C:21]1[C:22]([N:23]2[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[CH2:24]2)=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([OH:8])[C:10]3=[O:31]

Participants

5

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 226239512-Benzyloxy-5-bromo-6-(3-methyl-piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226239365-Bromo-2-hydroxy-6-(3-methylpiperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 97.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-benzyloxy-5-bromo-6-(3-methyl-piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.24 g, 0.50 mmol, from Example U1) in TFA (8.0 mL) at 0° C. was added a 1.0 M solution of boron tris(trifluoroacetate) in TFA (5 mL). The reaction was stirred at 0° C. for 2 hours, then poured into a solution of water/methanol (1:1), and extracted with chloroform. The organic layer was dried over MgSO4, filtered, and the solvent removed under vacuum to give 0.19 g of the title compound as the TFA salt, mp >250° C.

Workup

  1. customat 0° C.
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8f414f90e69046dbbb6856c6514c52e6
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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