Dimethylformamide → HCID 178521112, compound

HRID 1793399Notes

Reaction equation

HRID 1793399 reaction equation
[F:1][C:2]1[C:11]2[NH:10][CH:9]=[C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=4)[N:14]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:28])=O.CN(C)C=O>ClCCl>[F:1][C:2]1[C:11]2[NH:10][CH:9]=[C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([Cl:28])=[O:20])=[CH:17][CH:16]=4)[N:14]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178524449HCID 178524449, compound

Product 1

HCID 178521112HCID 178521112, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of finely ground 4-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoic acid (1.1 g. 3.4 mmol) in dichloromethane (6 ml) was added oxalyl chloride (2.4 ml, 29 mmol) followed by a drop of dimethyl formamide. The mixture was stirred under nitrogen at 45° C. for 3 h. The solvent was removed in vacuum to yield 4-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4, 3-c]quinolin-2-yl]-benzoyl chloride (1.15 g, quantitative) as a pale yellow solid that was used without further purification.

Workup

  1. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-de7f9117544941b58fe05a3b6a6abcd9
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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