p-Toluenesulfonic acid → Ammonium Hydroxide

HRID 2426158Notes

Reaction equation

HRID 2426158 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([CH2:12][C:13]([O:15]CC)=O)[C:5](=[O:11])[NH:6]2.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)=O>[NH4+:1].[OH-:11].[NH:6]1[C:7]2[C:3]3[CH:4]([CH2:12][C:13](=[O:15])[NH:1][C:2]=3[CH:10]=[CH:9][CH:8]=2)[C:5]1=[O:11]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86629728(+/-)-Ethyl (4-amino-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

Product 2

HCID 14923Ammonium HydroxideHCID 57663743(+/-)-2a,5-Dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (±)-ethyl (4-amino-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate from Step B (2.40 g, 10.2 mmol), p-toluenesulfonic acid (195 mg, 1.03 mmol) and AcOH (1 mL) was heated in xylenes (10 mL) at reflux for 24 h, then concentrated to dryness under reduced pressure. The crude product was partially purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:9:1, to give a crude sample of the title compound. Further purification was achieved by trituration with CH2Cl2 to give the title compound. MS: m/z=189 (M+1).

Workup

  1. temperatureat reflux for 24 h
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe crude product was partially purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-eb24e2186b9b4d789805b9f1718da129
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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