Ethyl chloroformate → 5h-Pyrrolo[1,2-b]cinnolin-10-one

HRID 1639249Notes

Reaction equation

HRID 1639249 reaction equation
F[C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[N:7]([NH:11]C(=O)OCC)[CH:8]=[CH:9][CH:10]=1)=[O:5].NN1C=CC=C1CC1C=CC=CC=1F.ClC(OCC)=O.[OH-].[K+]>C(O)C.O>[CH:10]1[CH:9]=[CH:8][N:7]2[C:6]=1[C:4](=[O:5])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[NH:11]2

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 13457759[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl esterHCID 198387701-Amino-2-(2-fluorobenzyl)pyrrole

Product 1

HCID 113213465h-Pyrrolo[1,2-b]cinnolin-10-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl ester (60.0 g, prepared from 1-amino-2-(2-fluorobenzyl)pyrrole and ethyl chloroformate in substantially the same manner as in Example 3) in 250 ml of ethanol was treated with a solution of potassium hydroxide (51 g) in 150 ml of water and then the mixture was heated at reflux for 1 hour. The ethanol was evaporated and the aqueous layer washed with 3×500 ml of ether. The aqueous phase was then adjusted to pH 5 with 6N HCl and the product collected by filtation. Oven drying yielded 20 g of a yellow powder, mp>300° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customThe ethanol was evaporated
  4. washthe aqueous layer washed with 3×500 ml of ether
  5. customthe product collected by filtation
  6. customOven drying

Sources & evidence

ORD record
ord-1830f54689b2455d846521cb8260a50c
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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