4-Aminobenzonitrile → HCID 178466668, compound

HRID 2104970

Reaction equation

HRID 2104970 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[CH:9]=O)[CH3:2].[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)/[CH:9]=[N:13]/[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 862472315-Ethoxy-2-fluorobenzaldehyde

Product 1

HCID 178466668HCID 178466668, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 53.1 (600 mg, 3.6 mmol) and 4-aminobenzonitrile (421 mg, 3.6 mmol) in toluene (50 mL) was refluxed in a Dean-stark apparatus for 4 h. The reaction mixture was the concentrated and the resulted solid was washed with hexane to obtained Intermediate 53.2 (700 mg, 80%). 1H NMR (CDCl3) δ 1.42 (t, 3H), 4.08 (q, 2H), 7.05 (m, 2H), 7.27 (d, J=8 Hz, 2H), 7.70 (d, J=8 Hz, 2H), 8.69 (s, 1H).

Workup

  1. temperaturewas refluxed in a Dean-stark apparatus for 4 h
  2. concentrationconcentrated
  3. washthe resulted solid was washed with hexane

Sources & evidence

ORD record
ord-9fc3cadaf645408c8caf0f590eb12f53
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Linked notes

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