Water → HCID 22623924, compound

HRID 279039Notes

Reaction equation

HRID 279039 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:12][CH:11]=[C:10]3[C:5]2=[C:6]([CH:22]=1)[C:7](=[O:21])[N:8]([OH:20])[C:9]3=[O:19].C1C(=O)N([Cl:30])C(=O)C1.O>C(O)(=O)C>[Br:1][C:2]1[CH:22]=[C:6]2[C:5]3=[C:10]([CH:11]=[C:12]([Cl:30])[C:13]([N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:4]3[CH:3]=1)[C:9](=[O:19])[N:8]([OH:20])[C:7]2=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 22623987HCID 22623987, compound

Product 1

HCID 22623924HCID 22623924, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-bromo-2-hydroxy-7-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.15 g, 0.42 mmol, from Example 59) and NCS (0.072 g, 0.54 mmol) in acetic acid (12 mL) was reacted at 100° C. for 3 hours. The reaction mixture was cooled and poured into water. The resulting precipitate was collected by filtration, washed with water, and dried to give 0.072 g of the title compound.

Workup

  1. customwas reacted at 100° C. for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-03549622173c42c0bf9bf3e3fe9397cf
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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