Sodium Acetate → N*2*-tert-Butyl-3-chlorobenzene-1,2-diamine

HRID 558962Notes

Reaction equation

HRID 558962 reaction equation
[C:1]([NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:15])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+]>CO.O.[Cl-].[Ti+3].[Cl-].[Cl-]>[C:1]([NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 10823273N-tert-Butyl-6-chloro-2-nitroaniline

Product 1

HCID 10845671N*2*-tert-Butyl-3-chlorobenzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of titanium (III) chloride (10 wt. % in 20-30% hydrochloric acid, 120 ml, 78 mmol) was added drop wise to a solution of tert-butyl-(2-chloro-6-nitrophenyl)-amine from Example 12A (5.7 g, 25 mmol) and sodium acetate (112 g, 1.4 moles) in methanol (205 ml) and water (63 ml). The mixture was stirred for 2 h, water was added to dissolve remaining solids and the organic solvent was evaporated. The mixture was neutralised with solid sodium hydrogen carbonate and extracted with EtOAc. The organic extracts were dried and evaporated to afford an orange oil; yield 4.7 g, 94%.

Workup

  1. dissolutionto dissolve
  2. customthe organic solvent was evaporated
  3. extractionextracted with EtOAc
  4. customThe organic extracts were dried
  5. customevaporated
  6. customto afford an orange oil

Sources & evidence

ORD record
ord-06d76078b39e45029c0bf77efcd7ed01
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

Loading…