Dimethylformamide → HCID 178521108, compound

HRID 1793392Notes

Reaction equation

HRID 1793392 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]1[C:17]2[NH:16][CH:15]=[C:14]3[C:18](=[O:30])[N:19]([C:21]4[CH:22]=C([CH:27]=[CH:28][CH:29]=4)C(O)=O)[N:20]=[C:13]3[C:12]=2[CH:11]=[CH:10][CH:9]=1.CN(C)C=O>ClCCl>[F:7][C:8]1[C:17]2[NH:16][CH:15]=[C:14]3[C:18](=[O:30])[N:19]([C:21]4[CH:22]=[C:1]([CH:27]=[CH:28][CH:29]=4)[C:2]([Cl:4])=[O:3])[N:20]=[C:13]3[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178524377HCID 178524377, compound2×

Product 1

HCID 178521108HCID 178521108, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Oxalyl chloride (20 ml, 0.2 mol) was added dropwise over 2 min to a stirred solution of 3-(6-fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (intermediate 3) (2.0 g, 6.1 mmol) in dichloromethane (10 ml) at room temperature. N,N-Dimethylformamide (50 μl) was then added and the resulting mixture heated to 50° C. for 1 h. The solution was then cooled to room temperature and then concentrated in vacuo to leave the title compound (intermediate 4) (2.0 g, 96%) as a beige solid.

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b99d872116fe4931a25f64e611601e06
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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