Ethanolamine → HC Yellow no. 13

HRID 920118Notes

Reaction equation

HRID 920118 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].F[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]>C1COCC1>[N+:16]([C:7]1[CH:8]=[C:9]([C:12]([F:13])([F:14])[F:15])[CH:10]=[CH:11][C:6]=1[NH:1][CH2:2][CH2:3][OH:4])([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 2799157HC Yellow no. 13Yield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminoethanol (1.76 g, 28.8 mmol) in THF (10 mL) was added 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (2.0 g, 9.6 mmol) at 0° C. The solution was allowed to warm to RT and stirred at RT for 2 h. Solvent was removed under reduced pressure, and the residue was diluted with EtOAc (100 mL) washed with brine (30 mL×3), dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (2.4 g, 100%), which was used in the next step without further purification. 1H NMR (600 MHz, CDCl3) δ 8.59-8.44 (m, 2H), 7.65 (dd, J=9.0, 2.2 Hz, 1H), 7.03 (d, J=9.0 Hz, 1H), 4.03-3.99 (m, 2H), 3.60-3.56 (m, 2H).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (100 mL)
  3. washwashed with brine (30 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f9e2ab5df994fdfb671f0fe0fc6da25
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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