4-Fluoroaniline → HCID 178522139, compound

HRID 1836426Notes

Reaction equation

HRID 1836426 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>CN(C=O)C>[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([SH:1])=[N:3][CH:4]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 1785245186-sulfanylpyridine-3-carboxylic acid

Product 1

HCID 178522139HCID 178522139, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-mercaptonicotinic acid (0.85 g, 5.48 mmol) in 50 mL of DMF was added 4-fluoroaniline (1.0 mL, 11.0 mmol) and 2-ethyoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ, 1.6 g, 6.6 mmol). The mixture was stirred for 30 minutes and the volatiles removed in vacuo. The resulting residue was diluted with ethyl acetate to yield a light tan solid that was isolated by vacuum filtration to give 0.63 g (47%) of the titled compound: 1H NMR (300 MHz, DMSO-d6) δ 10.20 (s, 1H), 8.28 (m, 1H), 7.83 (m, 1H), 7.68 (m, 2H), 7.33 (m, 1H), 7.15 (m, 2H); MS (EI) m/z 247.05 (M-H)−.

Workup

  1. customthe volatiles removed in vacuo
  2. additionThe resulting residue was diluted with ethyl acetate
  3. customto yield a light tan solid
  4. customthat was isolated by vacuum filtration

Sources & evidence

ORD record
ord-af6402df695e42fe973e74725f101018
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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