Ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate → Ethyl 3-[(2,6-diaminophenyl)amino]-2,2-difluoropropanoate

HRID 1628519Notes

Reaction equation

HRID 1628519 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH:13][CH2:14][C:15]([F:22])([F:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-])=O>O1CCCC1.[Pd]>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[C:5]=1[NH:13][CH2:14][C:15]([F:21])([F:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 86632898Ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate

Product 1

HCID 68739019Ethyl 3-[(2,6-diaminophenyl)amino]-2,2-difluoropropanoateYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate (2.44 g, 7.644 mmol) in tetrahydrofuran (50 mL) was added 10% palladium on carbon (50% wet; 588.0 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 16 hrs. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound as a pale yellow oil (2.00 g, 7.715 mmol, quant.).

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-871ef7d68aae4707927955b64ab04fdb
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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