Dimethylformamide → (5,7-Difluoro-quinolin-6-yl)-acetyl chloride

HRID 655247Notes

Reaction equation

HRID 655247 reaction equation
[F:1][C:2]1[C:11]([CH2:12][C:13](O)=[O:14])=[C:10]([F:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(Cl)(=O)C([Cl:20])=O.CN(C)C=O>ClCCl>[F:1][C:2]1[C:11]([CH2:12][C:13]([Cl:20])=[O:14])=[C:10]([F:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 577423352-(5,7-Difluoroquinolin-6-yl)acetic acid

Product 1

HCID 59320312(5,7-Difluoro-quinolin-6-yl)-acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5,7-Difluoro-quinolin-6-yl)-acetic acid (1 g, 4.48 mmol) was added to an oven-dried round-bottom flask and suspended in dichloromethane (18 ml) The suspension was maintained under nitrogen atmosphere and cooled to 0° C. Next, the oxalyl chloride (470 uL, 5.38 mmol) was added slowly, followed by a catalytic amount of dimethylformamide. The solution was allowed to warm to room temperature over 2 hours. The solution was then concentrated in vacuo and dried via azeotropic distillation with toluene to afford the title compound. ES-MS m/z: 238 (M+H+) of methyl ester.

Workup

  1. temperaturewas maintained under nitrogen atmosphere
  2. temperatureto warm to room temperature over 2 hours
  3. concentrationThe solution was then concentrated in vacuo
  4. dry with materialdried via azeotropic distillation with toluene

Sources & evidence

ORD record
ord-a9cc0a22ffbb4af1be561f616dd777ed
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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