Glycine ethyl ester, hydrochloride → 70656-89-2

HRID 1816899Notes

Reaction equation

HRID 1816899 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=O)[CH3:10].Cl.C([O:15][C:16](=O)[CH2:17][NH2:18])C>N1C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:16](=[O:15])[CH2:17][N:18]=[C:9]([CH3:10])[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 110747461-(2-Amino-5-bromophenyl)ethan-1-one

Product 1

HCID 13622716470656-89-2Yield 16.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(2-amino-5-bromo-phenyl)-ethanone (8 g, 37 mmol) and glycine ethyl ester hydrogen chloride (6.7 g, 48 mmol) in pyridine was heated at reflux for 24 hrs under nitrogen. The reaction mixture was cooled, solvent removed, and residue was treated with a saturated aqueous ammonium chloride solution (200 mL). Ethyl acetate (300 mL) was added and organic layer was separated, dried (MgSO4), concentrated, and the residue purified on silica gel column (hexane:ethyl acetate/1:1) to give 7-bromo-5-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one as a brown solid (1.51 g, 16%). 1H NMR (DMSO-d6): δ 10.49 (s, 1H), 7.92 (d, J=2.0 Hz, 1H), 7.66 (dd, J=8.7, 2.1 Hz, 1H), 7.08 (d, J=8.7 Hz, 1H), 3.91 (s, 2H), 2.39 (s, 3H). MS (ESI) m/z 253/255 ([M+H]+); Anal. calcd for C10H9BrN2O: C, 47.46; H, 3.58; N, 11.07. Found: C, 47.58; H, 3.52; N, 10.95.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hrs under nitrogen
  3. temperatureThe reaction mixture was cooled
  4. customsolvent removed
  5. additionresidue was treated with a saturated aqueous ammonium chloride solution (200 mL)
  6. additionEthyl acetate (300 mL) was added
  7. customorganic layer was separated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customthe residue purified on silica gel column (hexane:ethyl acetate/1:1)

Sources & evidence

ORD record
ord-33c9cc06b05b4c469442788c5b013e77
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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