Water → n,n-Bis(2,2,2-trifluoroethyl)-3-methyl-4-nitroaniline

HRID 1897845

Reaction equation

HRID 1897845 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[BH4-].[Na+].O.[F:15][C:16]([F:21])([F:20])[C:17](O)=O>>[F:15][C:16]([F:21])([F:20])[CH2:17][N:5]([CH2:17][C:16]([F:21])([F:20])[F:15])[C:4]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 118984-Nitro-m-toluidineHCID 4311764Sodium borohydride

Product 1

HCID 11243980n,n-Bis(2,2,2-trifluoroethyl)-3-methyl-4-nitroanilineYield 82%

Conditions

Temperature
60 °C

Procedure

3-Methyl-4-nitroaniline 3.9 g (25 mmol) was dissolved in 100 mL of trifluoroacetic acid with stirring under N2 at 60° C. Next, sodium borohydride pellets (14 g, 15 eq.) were added portionwise. Ten minutes after the addition of the pellets, the reaction was heated to 90° C. After 12 h at 90° C., the reaction was cooled, added slowly to water, and then filtered. The resulting solid filtrate was washed first with water and then with hexanes and was then dried. This procedure resulted in 6.6 g (82% yield) of a light yellow powder. Data for compound 101: 1H-NMR (CDCl3, 500 MHz) 8.10 (d, 1H, J=9.3 Hz), 6.78 (dd, 1H, J=9.3 and 2.9 Hz), 6.72 (d, 1H, J=2.9 Hz), 4.13 (q, 4H, J=8.4 Hz), 2.66 (s, 3H).

Workup

  1. additionTen minutes after the addition of the pellets
  2. temperaturethe reaction was heated to 90° C
  3. temperaturethe reaction was cooled
  4. filtrationfiltered
  5. washThe resulting solid filtrate was washed first with water
  6. dry with materialwith hexanes and was then dried

Sources & evidence

ORD record
ord-ed3f009998e4416782f7f266fdfcec8e
Source dataset
uspto-grants-2013_08
Patent number
US08519158B2

Linked notes

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