Ethanolamine → HC Yellow no. 13

HRID 273362Notes

Reaction equation

HRID 273362 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 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-aminoethanol (5 ml, 150 mmol) in THF (20 ml), 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (6.9 ml, 50 mmol) was added slowly at 0° C. After the completion of the addition, the reaction mixture was stirred at RT for 24 hrs. THF was evaporated using a rotary evaporator and the residue was extracted using water and ethyl acetate. Ethyl acetate was washed with more water, dried and evaporated to give crystalline 2-aminoethanol derivative (10.0 g, 80%).

Workup

  1. additionAfter the completion of the addition
  2. customTHF was evaporated
  3. customa rotary evaporator
  4. extractionthe residue was extracted
  5. washEthyl acetate was washed with more water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d22f97bcb5f74a9683f0c90a18a38335
Source dataset
uspto-grants-2008_11
Patent number
US07456293B2

Reaction notes

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