3-(Trifluoromethyl)aniline → HCID 178468887, compound

HRID 1352912Notes

Reaction equation

HRID 1352912 reaction equation
[O:1]=[C:2]1[C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][C:13]1[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=1.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>C(Cl)(Cl)Cl>[O:1]=[C:2]1[N:3]([CH2:12][C:13]2[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=2)[C:4]2[C:9](/[C:10]/1=[N:28]/[C:27]1[CH:29]=[CH:30][CH:31]=[C:25]([C:24]([F:23])([F:32])[F:33])[CH:26]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 4331211HCID 4331211, compound

Product 1

HCID 178468887HCID 178468887, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 5-[(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)methyl]-2-furoate (60 mg, 0.200 mmol) and 3-trifluoromethylaniline (32 mg, 0.200 mmol) was heated at 140° C. for 2 h. The residue was dissolved in CHCl3 (1 mL) and purified by preparative TLC using EtOAc/hexane (6:4), giving the desired product (20 mg, 23%).

Workup

  1. custompurified by preparative TLC

Sources & evidence

ORD record
ord-7c59d8d8ea2a43e3843be666241d5825
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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