2-(Trifluoromethyl)aniline → HCID 178427870, compound

HRID 1370344Notes

Reaction equation

HRID 1370344 reaction equation
[CH3:1][CH:2]([C:8]([C:10]([F:13])([F:12])[F:11])=O)[C:3]([O:5]CC)=O.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>O>[F:13][C:10]([F:11])([F:12])[C:8]1[C:2]([CH3:1])=[C:3]([OH:5])[C:19]2[C:17](=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:22]=[CH:21][CH:20]=2)[N:18]=1

Participants

4

Reactant 2

HCID 69222-(Trifluoromethyl)anilineHCID 2737204Ethyl 2-methyl-4,4,4-trifluoroacetoacetate

Product 1

HCID 178427870HCID 178427870, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To polyphosphoric acid (101 g) heated to 75° C. was added ethyl 2-methyl-4,4,4-trifluoroacetoacetate (10.0 g, 50.5 mmol). 2-Trifluoromethylaniline (6.0 mL, 48.1 mmol) was added dropwise and the reaction mixture heated to 120° C. for 6 h, cooled in ice and treated with water. The cream precipitate was filtered and washed with water and heptane to afford the product (11.4 g, 80%) as a white solid: mp 116.2-116.8° C.; IR νmax (Nujol)/cm−1 3440, 2924, 2854, 1624, 1612, 1584, 1458, 1330, 1226, 1142, 1109; NMR δH (400 MHz, CDCl3) 2.29 (3H, s), 7.47 (1H, t, J 7.6 Hz), 7.98 (1H, d, J 7.6 Hz), 8.60 (1H, d, J 7.4 Hz).

Workup

  1. temperaturecooled in ice
  2. filtrationThe cream precipitate was filtered
  3. washwashed with water and heptane

Sources & evidence

ORD record
ord-2c76148677bc478bbc37514df5a154f4
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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