Water → 9-Hydroxy-9,12-dihydro-7H-cyclopenta[6,7]indolizino[1,2-b]-quinoline-7,10(8H)-dione

HRID 1635075Notes

Reaction equation

HRID 1635075 reaction equation
[H-].[Na+].[Li+].[Br-].Br[C:6]1[C:15]([CH2:16]Br)=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.[OH2:18].CO[CH2:21][CH2:22][O:23]C.[CH3:25][N:26]([CH:28]=[O:29])C>>[OH:23][CH:22]1[C:21]2[C:28](=[O:29])[N:26]3[C:25](=[CH:10][C:9]=2[C:8](=[O:18])[CH2:13]1)[C:6]1=[N:7][C:8]2[C:13]([CH:14]=[C:15]1[CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 5

HCID 962WaterHCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 6133242-Bromo-3-(bromomethyl)quinolineHCID 18463208dimethoxyethane N,N-dimethylformamide

Product 1

HCID 98829159-Hydroxy-9,12-dihydro-7H-cyclopenta[6,7]indolizino[1,2-b]-quinoline-7,10(8H)-dione

Conditions

Temperature
80 °C

Procedure

0.6 mmol (18 mg) of NaH as an 80% dispersion in mineral oil is added in small fractions to a solution, stirred at 0° C., of 0.6 mmol (100 mg) of the compound described in Preparation A in 20 ml of a DME/DMF mixture (16/4 (v/v)). The mixture is stirred at 0° C. for 10 minutes before the addition, at that temperature, of 2.4 mmol (210 mg) of LiBr. After returning to room temperature, the reaction mixture is stirred for ¼ hour before the addition of 0.66 mmol (200 mg) of 2-bromo-3-bromomethylquinoline. The reaction mixture is then heated at 80° C. for 20 hours and, after returning to room temperature, subsequently poured into a large excess of water. The precipitate that forms is filtered off and washed with ether to yield the expected product.

Workup

  1. customAfter returning to room temperature
  2. customafter returning to room temperature
  3. filtrationThe precipitate that forms is filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-8ef1e457b7454c29911682cc82bda246
Source dataset
uspto-grants-2003_01
Patent number
US06509345B2

Reaction notes

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