3-Chloro-4-fluoroaniline → HCID 178471936, compound

HRID 1170458Notes

Reaction equation

HRID 1170458 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:19])[C:9](=[CH:15][N:16]([CH3:18])C)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Cl:20][C:21]1[CH:22]=C([CH:25]=[CH:26][C:27]=1[F:28])N>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:19])[C:9](=[CH:15][NH:16][C:18]1[CH:25]=[CH:26][C:27]([F:28])=[C:21]([Cl:20])[CH:22]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 54509863Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 178471936HCID 178471936, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-chloro-α-[(dimethylamino)methylene]-β-oxo-benzenepropanoate (50 mg, 0.177 mmol) in 1 mL of EtOH was treated with neat 3-chloro-4-fluoroaniline (25.8 mg, 0.177 mmol). After stirring at rt until complete by TLC, the reaction was concentrated in vacuo. The residue was subjected to flash chromatography (1:1 EtOAc/hexanes), affording 42.6 mg (63%) of the product as a white solid, mp 96-102° C. 1H NMR (400 MHz, CDCl3 9:1 ratio of alkene isomers, major isomer NMR given) δ12.66 (d, 1H, J=12.8 Hz), 8.50 (d, 1H, J=13.2 Hz), 7.37-7.16 (m, 7H), 4.01 (q, 2H, J=7.1 Hz), 0.93 (t, 2H, J=7.1 Hz).

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-e888cc73a6644e0a982c523511c6c195
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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