Triethylamine → 2-Benzyloxy-5-bromo-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278967Notes

Reaction equation

HRID 278967 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:26])[C:22]([N+:23]([O-])=O)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1[CH2:32][CH2:31][CH2:30][CH2:29]1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:26])[C:22]([N:23]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 226239822-Benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239162-Benzyloxy-5-bromo-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione (0.25 g, 0.59 mmol, from Example S1-A) in DMF (5 mL) was added pyrrolidine (0.05 g, 0.70 mmol) and triethyl amine (0.18 g, 1.8 mmol). The reaction was reacted at 85° C. for 24 hours, cooled, and concentrated under vacuum. The residue was triturated with methanol to give 0.24 g of the title compound.

Workup

  1. customThe reaction was reacted at 85° C. for 24 hours
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-eb24fd927915489195edf2ff3deffa06
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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