p-Toluenesulfonic acid → Ammonium Hydroxide

HRID 551005Notes

Reaction equation

HRID 551005 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=289 (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-7a807e01bc76455d9aadc3fb8cded40a
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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