Ammonium Chloride → HCID 21966476, compound

HRID 2212599Notes

Reaction equation

HRID 2212599 reaction equation
[CH2:1]([N:8]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([CH3:22])=[CH:16][C:15]=1Br)[C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH2:1]([N:8]1[C:14]2[C:15](=[CH:16][C:17]([CH3:22])=[C:18]([O:20][CH3:21])[CH:19]=2)[C:10]([CH3:12])([CH3:11])[C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 21966456HCID 21966456, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 21966476HCID 21966476, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 75806TricyclohexylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-benzyl-N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (4.35 g, 11.56 mmol) in 1,4-dioxane (115 mL) was added sodium tert-butoxide (1.66 g, 17.34 mmol). The mixture was degassed under argon for 30 minutes, then palladium (II) acetate (130 mg, 0.58 mmol) and tricyclohexylphosphine (162 mg, 0.58 mmol) were added and the mixture refluxed overnight. A solution of saturated aqueous ammonium chloride was added and the solution extracted with ethyl acetate. The organic extract was washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 1.94 g of 1-benzyl-6-methoxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (57% yield). 1H NMR (300 MHz; CDCl3): 1.40 (s, 6 H), 2.16 (s, 3 H), 3.67 (s, 3 H), 4.90 (s, 2 H), 6.26 (s, 1 H), 6.96 (s, 1 H), 7.27 (m, 5 H).

Workup

  1. customThe mixture was degassed under argon for 30 minutes
  2. temperaturethe mixture refluxed overnight
  3. extractionthe solution extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed successively with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-34685d1e9b1a4f97bd8ad646afd86969
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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