Iodoethane → HCID 86739199, compound

HRID 2296356Notes

Reaction equation

HRID 2296356 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH:4]=[C:5]1[C:9]2=[N:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([OH:21])=[O:20])=[CH:15][C:16]=3[C:17](=[O:18])[N:8]2[CH2:7][CH2:6]1.[CH2:26](I)[CH3:27].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH:4]=[C:5]1[C:9]2=[N:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([O:21][CH2:26][CH3:27])=[O:20])=[CH:15][C:16]=3[C:17](=[O:18])[N:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 53937337HCID 53937337, compound

Product 1

HCID 86739199HCID 86739199, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-pyrrolo[2,1-b]quinazoline-7-carboxylic acid (1 g) was reacted with ethyl iodide (0.93 g) and anhydrous K2CO3 (0.83 g) in dimethylformamide (10 ml) under stirring at room temperature for 16 hours. After dilution with ice water the precipitate was filtered and washed with water until neutral: crystallization from chloroform-ethanol gave 0.9 g of 3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-pyrrolo[2,1-b]quinazoline-7-carboxylic acid, ethyl ester, m.p. 184°-185° C.

Workup

  1. filtrationAfter dilution with ice water the precipitate was filtered
  2. washwashed with water until neutral:
  3. customcrystallization from chloroform-ethanol

Sources & evidence

ORD record
ord-afc023879a744a9fbf1f313de4317374
Source dataset
uspto-grants-1984_01
Patent number
US04428952

Reaction notes

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