3-(2-Fluoro-6-nitrophenylamino)propionic acid methyl ester → 6-Fluoro-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one

HRID 558949Notes

Reaction equation

HRID 558949 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:8]=1[F:16]>CO.[Pd]>[F:16][C:8]1[C:7]2[NH:6][CH2:5][CH2:4][C:3](=[O:2])[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 574707783-(2-Fluoro-6-nitrophenylamino)propionic acid methyl ester

Product 1

HCID 231111066-Fluoro-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of 3-(2-fluoro-6-nitrophenylamino)propionic acid methyl ester from Example 1A (650 mg, 2.7 mmol) in methanol (40 ml) was added palladium on carbon (10%, 200 mg). Hydrogen gas was bubbled through the mixture for two hours, filtered through Celite® and reduced in vacuo. The residue was dissolved in propan-2-ol (20 ml) and to it was added acetic acid (2 ml). The mixture was stirred for 18 h, heated at reflux for 2 h, cooled, reduced in vacuo and azeotroped with toluene; yield 480 mg, 99%.

Workup

  1. customHydrogen gas was bubbled through the mixture for two hours
  2. filtrationfiltered through Celite®
  3. dissolutionThe residue was dissolved in propan-2-ol (20 ml) and to it
  4. additionwas added acetic acid (2 ml)
  5. temperatureheated
  6. temperatureat reflux for 2 h
  7. temperaturecooled
  8. customazeotroped with toluene

Sources & evidence

ORD record
ord-74543a84b73b451684658a395948c639
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

Loading…