3-(Trifluoromethyl)aniline → HCID 135485505, compound

HRID 1374969Notes

Reaction equation

HRID 1374969 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=[O:17])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>C(Cl)Cl.C(O)(=O)C>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[N:24][C:23]3[CH:25]=[CH:26][CH:27]=[C:21]([C:20]([F:19])([F:28])[F:29])[CH:22]=3)[C:7](=[O:17])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 21079385HCID 21079385, compound

Product 1

HCID 135485505HCID 135485505, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-hydroxy-1-phenyl-1H-indole-2,3-dione (13 mg, 0.054 mmol) and 3-(trifluoromethyl)aniline (160 mg, 1 mmol) in CH2Cl2 (1 mL) and acetic acid (1 drop) was heated at 140° C. The crude product was purified preparative TLC [Eluent: EtOAc/hexane (2:3)], giving the desired product (3.5 mg, 17%).

Workup

  1. customThe crude product was purified preparative TLC [Eluent: EtOAc/hexane (2:3)]

Sources & evidence

ORD record
ord-41b6bcf68a474afea13a9d774ecc1c48
Source dataset
uspto-grants-2007_01
Patent number
US07166635B2

Reaction notes

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