Acetic Acid → ethyl 2-(4-fluoroanilino)acetate

HRID 356661Notes

Reaction equation

HRID 356661 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][NH:13][C:12]1[CH:14]=[CH:15][C:9]([F:8])=[CH:10][CH:11]=1)[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 70211Ethyl oxoacetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 711751ethyl 2-(4-fluoroanilino)acetateYield 65.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of ethyl glyoxylate (2.47 g, 0.024 mol) in 1,2-dichloroethane (30 mL) under argon at room temperature was treated succesively with 4-fluoroaniline (1.80 g, 0.016 mol), sodium triacetoxyborohydride (5.12 g, 0.024 mol) and acetic acid (1 mL). After stirring for two hours, the mixture was concentrated, dissolved in ethyl acetate and washed 5% sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic solution was concentrated and crystallized from ether/hexanes to give the title product (2.07 g, 65%) as a colorless solid, mp 72°-73° C. Analysis calculated for C10H12 FNO2 ·0.07 H2O: C, 60.54; H, 6.16; N, 7.06; F, 9.58. Found: C, 60.75; H, 6.15; N, 6.96; F, 9.13.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed 5% sodium bicarbonate, water and brine
  4. dry with materialThe dried (anhydrous magnesium sulfate) organic solution
  5. concentrationwas concentrated
  6. customcrystallized from ether/hexanes

Sources & evidence

ORD record
ord-9926b852089f46338ad494bacf291f18
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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