Aniline → N-Phenylglycine ethyl ester

HRID 1664493Notes

Reaction equation

HRID 1664493 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(#N)C>[C:2]1([NH:1][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 75190N-Phenylglycine ethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Kotake et al. (Chem. Pharm. Bull. 1995, 43, 829-841), a stirred solution of aniline (15.3 g, 0.16 mol) and DIEA (56 ml, 0.33 mol) in acetonitrile (120 ml) is heated to 60° C. and ethyl bromoacetate (18.2 ml, 0.16 mmol) is added dropwise within 2 h. The reaction mixture is kept stirring at this temperature for another 3 h and is then evaporated to dryness. Water is added to the residue, the solid is filtered and thoroughly rinsed with H2O. Crystallization from toluene provided pure subtitle compound as beige crystals (25.5 g) in 87% yield. tR (LC-3) 2.33 min; ESI-MS (positive ion): m/z 180.27 [M+H]+ (calcd 179.22 for C10H13NO2). 1H-NMR (CDCl3): 1.29 (t, J=7.0 Hz, 3H); 3.90 (s, 2H); 4.25 (m, 3H); 6.61 (d, J=8.2 Hz, 2H); 6.75 (t, J=7.1 Hz, 1H); 7.21 (m, 2H).

Workup

  1. customis then evaporated to dryness
  2. additionWater is added to the residue
  3. filtrationthe solid is filtered
  4. washthoroughly rinsed with H2O
  5. customCrystallization from toluene provided pure subtitle compound as beige crystals (25.5 g) in 87% yield
  6. customtR (LC-3) 2.33 min

Sources & evidence

ORD record
ord-1d6983bd78c14a8ea1870026fb13708e
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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