Sodium Sulfate → Ethyl 2-(2,2-difluoroethoxy)-4-methylamino-5-amino-benzoate

HRID 410098Notes

Reaction equation

HRID 410098 reaction equation
[F:1][CH:2]([F:21])[CH2:3][O:4][C:5]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>[Ni].C1COCC1>[NH2:18][C:13]1[C:14]([NH:16][CH3:17])=[CH:15][C:5]([O:4][CH2:3][CH:2]([F:21])[F:1])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 59529798Ethyl 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoate

Product 1

HCID 59529827Ethyl 2-(2,2-difluoroethoxy)-4-methylamino-5-amino-benzoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoate (2.0 g; 6.57 mmol), RaNi (1.0 g) and THF (100 mL) is stirred under H2-atmosphere (8 atm) overnight at rt. Na2SO4 is added and the mixture is stirred another 30 min under H2-atmosphere. The mixture is filtered through celite and concentrated and the sub-title compound is used in the next step without further purification.

Workup

  1. stirringthe mixture is stirred another 30 min under H2-atmosphere
  2. filtrationThe mixture is filtered through celite and
  3. concentrationconcentrated
  4. customthe sub-title compound is used in the next step without further purification

Sources & evidence

ORD record
ord-08d7e03df07a49da8cbb79d6517aa1cb
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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