Dimethylformamide → HCID 86667818, compound

HRID 1615689Notes

Reaction equation

HRID 1615689 reaction equation
[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)[N:4]=[C:3]1[CH:15]([CH3:20])[CH2:16][C:17](O)=[O:18].CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl>[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)[N:4]=[C:3]1[CH:15]([CH3:20])[CH2:16][C:17]([Cl:29])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68089228HCID 68089228, compound

Product 1

HCID 86667818HCID 86667818, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)butanoic acid (200 mg, 0.74 mmol) in oxalyl chloride (8 mL) and DCM (8 mL) was added DMF (5 mg). The mixture was stirred at room temperature for 2 h. The mixture was concentrated to dryness to give the product as a yellow solid (160 mg, 75% yield). See, e.g., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2000, 294-296; Tetrahedron Letters, 2000, 4165-4168.

Workup

  1. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-21fbcb8e1fc346c99dad089e9d92fb0e
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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