HCID 70978766, compound → HCID 86718494, compound

HRID 1485397Notes

Reaction equation

HRID 1485397 reaction equation
[CH2:1]([N:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)[C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[NH4+].[Cl-].[Fe]>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 1

HCID 70978766HCID 70978766, compound

Product 1

HCID 86718494HCID 86718494, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

Iron powder (3 g) was added to a solution of methyl 3-(benzyl(2-nitrophenyl)amino)-3-oxopropanoate (400 mg, 1.22 mmol) in EtOH (10 mL) and NH4Cl (10 mL). The reaction mixture was heated at 70° C. for 2 h. The mixture was filtered off and the filtrate was extracted by EA (50 mL), the separated organic layer was dried over Na2SO4. After the solvent was removed in vacuum, the residue was purified by combi-flash to give methyl 3-((2-aminophenyl)(benzyl)amino)-3-oxopropanoate as a yellow solid (200 mg, 55%). LRMS (M+H)+: 298 m/z.

Workup

  1. filtrationThe mixture was filtered off
  2. extractionthe filtrate was extracted by EA (50 mL)
  3. dry with materialthe separated organic layer was dried over Na2SO4
  4. customAfter the solvent was removed in vacuum
  5. customthe residue was purified by combi-flash

Sources & evidence

ORD record
ord-3164b6082f3147d58798d3a9e8213311
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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