(+/-)-Ethyl (4-amino-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate → Ammonium Hydroxide

HRID 1696416Notes

Reaction equation

HRID 1696416 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:13][C:14]([O:16]CC)=O)([CH3:12])[C:5](=[O:11])[NH:6]2>CC(O)=O>[NH4+:1].[OH-:11].[CH3:12][C:4]12[C:5](=[O:11])[NH:6][C:7]3[C:3]1=[C:2]([CH:10]=[CH:9][CH:8]=3)[NH:1][C:14](=[O:16])[CH2:13]2

Participants

4

Reactant 1

HCID 86629727(+/-)-Ethyl (4-amino-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

Product 2

HCID 14923Ammonium HydroxideHCID 576637492a-Methyl-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-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate from Step B (2.37 g, 9.56 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 by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 0:100, gave the title compound. MS: m/z=203 (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-845087afe9c54fe38a830250347dc48d
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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