Hydrogen Bromide → HCID 10095397, compound

HRID 1110020Notes

Reaction equation

HRID 1110020 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:19]3[C:20]4[C:15]([CH2:16][CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[C:10]=2[CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=3)[CH2:25][CH2:24]2)=[CH:5][CH:4]=1.Br.[OH-].[Na+]>C(O)(=O)C.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:19]3[C:20]4[C:15]([CH2:16][CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[C:10]=2[CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=3)[CH2:27][CH2:28]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 10389831HCID 10389831, compound

Product 1

HCID 10095397HCID 10095397, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

7.5 g of 2-(4-methoxyphenyl)-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (preparation see Example 7) were dissolved in 110 ml of acetic acid. 110 ml of 41% strength aqueous hydrobromic acid were added to the solution, and the reaction mixture was heated under reflux for 16 hours. To work up the reaction mixture it was cooled to room temperature, then diluted with 100 ml of water and neutralized by addition of 10% strength aqueous sodium hydroxide solution (pH=6). It was then extracted with dichloromethane, and the organic phase was separated, dried and concentrated. The oily residue which remained was crystallized from ethanol/ether. 5.2 g of 2-(4-hydroxyphenyl)-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline having a melting point of 220° C. were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 16 hours
  3. extractionIt was then extracted with dichloromethane
  4. customthe organic phase was separated
  5. customdried
  6. concentrationconcentrated
  7. customThe oily residue which remained was crystallized from ethanol/ether

Sources & evidence

ORD record
ord-18b7262990714da6b4889c03bf4a3288
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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