Cyclopropanecarbonyl chloride → HCID 45588498, compound

HRID 2045923Notes

Reaction equation

HRID 2045923 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1>N1C=CC=CC=1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:21]([CH:18]2[CH2:20][CH2:19]2)=[O:22])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 45588498HCID 45588498, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 0.01 mol) in pyridine (10 mL) was cooled to 0° C. and cyclopropanecarbonyl chloride (0.91 mL, 0.01 mol) was added dropwise over 10 min. The reaction mixture was stirred overnight at room temperature, diluted with water (50 mL) and stirred for 30 min. The resulting solid was filtered, dried, and recrystallized from toluene to afford N-[3-(quinoxalin-2-yl)phenyl]cyclopropanecarboxamide (2.0 g, 69% yield). LCMS calculated for C18H15N3O (M+H): 290.34. found 290. 1H-NMR (DMSO-d6, 250 Mhz) δH: 10.45 (1H, br. s), 9.48 (1H, s), 8.52 (1H, s), 8.20-8.05 (2H, m), 8.05-7.80 (4H, m), 7.50 (1H, m), 1.90-1.75 (1H, m), 1.40-1.32 (4H, m).

Workup

  1. stirringstirred for 30 min
  2. filtrationThe resulting solid was filtered
  3. customdried
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b3046ef601bc4748ae144d97e4ac2e29
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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