4-Chloro-5-(3,3-difluoropyrrolidin-1-yl)-2-nitroaniline → 4-Chloro-5-(3,3-difluoropyrrolidin-1-yl)benzene-1,2-diamine dihydrochloride

HRID 1258636Notes

Reaction equation

HRID 1258636 reaction equation
[Cl:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10]2)=[CH:7][C:5]([NH2:6])=[C:4]([N+:16]([O-])=O)[CH:3]=1>[Pd].C1COCC1>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:6])=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10]1

Participants

4

Reactant 1

HCID 679578464-Chloro-5-(3,3-difluoropyrrolidin-1-yl)-2-nitroaniline

Product 1

HCID 679580194-Chloro-5-(3,3-difluoropyrrolidin-1-yl)benzene-1,2-diamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-5-(3,3-difluoropyrrolidin-1-yl)-2-nitroaniline (300 mg, 1.1 mmol), THF (10 mL) and Pd/C (20 mg) was stirred for 1.5 days at RT under a hydrogen atmosphere (3.0 bar). The catalyst was removed by filtration. To the filtrate was added 4 M HCl in dioxane (10 mL). The mixture was concentrated and used in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. additionTo the filtrate was added 4 M HCl in dioxane (10 mL)
  3. concentrationThe mixture was concentrated
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-d3a0e1a11a8c4d2ea6a32455eb846de4
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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