O-p-methoxybenzyl-N,N'-diisopropylisourea → 9-Chloro-6-fluoro-4-(p-methoxy benzyloxy)benzo[g]isoquinoline-5,10-dione

HRID 234821Notes

Reaction equation

HRID 234821 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[N:11][CH:10]=[C:9]([OH:17])[C:8]=3[C:7](=[O:18])[C:6]=2[C:5]([F:19])=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:38]=[CH:37][C:25]([CH2:26]OC(=NC(C)C)NC(C)C)=[CH:24][CH:23]=1>ClCCl>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[N:11][CH:10]=[C:9]([O:17][CH2:26][C:25]4[CH:37]=[CH:38][C:22]([O:21][CH3:20])=[CH:23][CH:24]=4)[C:8]=3[C:7](=[O:18])[C:6]=2[C:5]([F:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10563595O-p-methoxybenzyl-N,N'-diisopropylisoureaHCID 153619399-Chloro-6-fluoro-4-hydroxybenzo[g]isoquinoline-5,10-dione

Product 1

HCID 153619409-Chloro-6-fluoro-4-(p-methoxy benzyloxy)benzo[g]isoquinoline-5,10-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-chloro-6-fluoro-4-hydroxybenzo[g]isoquinoline-5,10-dione of Preparative Example 28 (0.050 g) and O-p-methoxybenzyl-N,N'-diisopropylisourea prepared in Step a (0.095 gs) in dichloromethane (1 mL) is stirred at room temperature for 3.5 h under a nitrogen blanket. The dark reddish-brown mixture is purified by flash chromatography over silica gel using gradient elution commencing with 100:2 (300 mL) followed by 100:4 (300 mL) mixtures of chloroform: tert-butyl methyl ether. Removal of the eluent yields 9-chloro-6-fluoro-4-(p-methoxy benzyloxy)benzo[g]isoquinoline-5,10-dione as a yellow-brown solid (0.032 g.)

Workup

  1. customis stirred at room temperature for 3.5 h under a nitrogen
  2. customThe dark reddish-brown mixture is purified by flash chromatography over silica gel using gradient elution commencing with 100:2 (300 mL)
  3. customRemoval of the eluent

Sources & evidence

ORD record
ord-27496d985bb2446d8a8d662eda5f797d
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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