Ammonium Chloride → Racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-one

HRID 2065392Notes

Reaction equation

HRID 2065392 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH:12]([CH2:18][N+:19]([O-])=O)[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.[Zn]>[NH2:19][CH2:18][CH:12]([CH:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:11])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58398993Racemic 6-chloro-3-(3,3-dimethyl-1-nitromethyl-butyl)-1,3-dihydro-indol-2-one

Product 1

HCID 58399003Racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-oneYield 100.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of racemic 6-chloro-3-(3,3-dimethyl-1-nitromethyl-butyl)-1,3-dihydro-indol-2-one (3.8 g, 12 mmol) in methanol (80 mL) was added an aqueous solution (20 mL) of ammonium chloride (6.5 g, 122 mmol), followed by the addition of Zinc (Aldrich, activated) (8 g, 122 mmol). The reaction mixture was stirred at room temperature for 0.5 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to a small volume, then the residue was partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated to give racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-one as a white foam (3.4 g, 99%)

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated to a small volume
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-42e67fbbd84d4197a03c6ce7f7d4355f
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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