Hydrochloric Acid → 9-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide

HRID 2379592Notes

Reaction equation

HRID 2379592 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[N:11][CH3:12])=[CH:4][CH:3]=1.Cl.[OH-].[Na+].[C:16](=[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20])=[O:17].N12CCCC1=NCCC2>C1(C)C=CC=CC=1.O>[OH-:17].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N+:7]3[C:16]([OH:17])=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19](=[O:20])[N:11]([CH3:12])[C:8]=32)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 107737343-Oxo-2-phenylprop-2-enoyl chlorideHCID 1356242226-Chloro-1-(methylimino)isoindoline

Product 1

HCID 1784798909-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxideYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 5.42 g of 6-chloro-1-(methylimino)isoindoline (prepared from the hydrochloride by treatment with 1.5 equivalents of 2N sodium hydroxide solution) and 120 ml of toluene was treated dropwise under argon at 0°-5° within 10 minutes with 5.96 g of α-carbonyl-phenylacetyl chloride. The mixture was stirred for 30 minutes, 4.47 g of 1,5-diazabicyclo[4.3.0]non-5-ene in 30 ml of toluene were subsequently added dropwise thereto, the mixture was stirred at 0°-5° for a further 90 minutes, then treated with 50 ml of water and the separated crystals were filtered off under suction and washed with 35 ml of methylene chloride and, after drying, there was obtained 3.66 g of 9-chloro1, 2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide (internal salt) with a m.p. of 245° (decomposition). This product was recrystallized from N,N-dimethylformamide and then had a m.p. of 288°.

Workup

  1. stirringthe mixture was stirred at 0°-5° for a further 90 minutes
  2. filtrationthe separated crystals were filtered off under suction
  3. washwashed with 35 ml of methylene chloride
  4. customafter drying

Sources & evidence

ORD record
ord-f4d0552517e646d08880dcd28e0a7952
Source dataset
uspto-grants-1994_11
Patent number
US05362738

Reaction notes

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