4-Fluoroaniline → HCID 2653166, compound

HRID 859162Notes

Reaction equation

HRID 859162 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([F:11])=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 2653166HCID 2653166, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-chloronicotinoyl chloride (10.5 g, 59.7 mmole) in dry dichloromethane (100 mL) was added 4-fluoroaniline (5.6 mL, 59.7 mmole), followed by the dropwise addition of N,N-diisopropylethylamine (21 mL, 119 mmol). After stirring for 90 minutes at room temperature, the mixture was diluted with ethyl acetate (20 mL) and washed with water. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by recrystallization using ethyl acetate/hexanes gave 13.8 g (92%) of a white solid. 1H NMR (300 MHz, CDCl3) δ 7.09–7.12 (m, 2H), 7.47–7.50 (m, 1H), 7.56–60 (m, 2H), 7.7 (bs, 1H), 8.15–8.18 (m, 1H), 8.84 (m, 1H); MS (EI) m/z 251.13 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. customby recrystallization

Sources & evidence

ORD record
ord-4434ff62262549c68f6da765ffed5213
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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