Methyl iodide → 5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

HRID 2291986Notes

Reaction equation

HRID 2291986 reaction equation
FC1C=CC=CC=1C(C1N(CNC(=O)OCC)C=CC=1)=O.F[C:23]1[CH:41]=[CH:40][CH:39]=[CH:38][C:24]=1[C:25]([C:27]1[N:28]([NH:32][C:33](=O)OCC)[CH:29]=[CH:30][CH:31]=1)=[O:26].CI.[OH-].[Na+]>C(O)C>[CH3:33][N:32]1[C:23]2[CH:41]=[CH:40][CH:39]=[CH:38][C:24]=2[C:25](=[O:26])[C:27]2=[CH:31][CH:30]=[CH:29][N:28]12

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13457759[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl esterHCID 86127982[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]methylcarbamic acid, ethyl ester

Product 1

HCID 141715685-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]methylcarbamic acid, ethyl ester (23.5 g, prepared from [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl ester and methyl iodide in substantially the same manner as in Example 4) and sodium hydroxide (12.0 g) in 140 mL of 50% aqueous ethanol was refluxed under N2 for 16 h. Evaporation of the volatiles left a bright yellow solid which was diluted with 300 ml of H2O and extracted with two 200 mL portions of dichloromethane. The organic extracts were dried (MgSO4), filtered and concentrated. The residue was recrystallized from dichloromethane to give 8.0 g of bright yellow crystals, mp 154°-156° C.

Workup

  1. temperaturewas refluxed under N2 for 16 h
  2. customEvaporation of the volatiles
  3. waitleft a bright yellow solid which
  4. additionwas diluted with 300 ml of H2O
  5. extractionextracted with two 200 mL portions of dichloromethane
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-c9e053db4a124a39aa7935070b5f1ab6
Source dataset
uspto-grants-1989_01
Patent number
US04800203

Reaction notes

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