Sulfuric Acid → 5-ethyl-2,3-dihydro-1H-indole-2,3-dione

HRID 1672328Notes

Reaction equation

HRID 1672328 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].Cl[C:11](Cl)(Cl)[CH:12]([OH:14])O.S([O-])([O-])(=O)=[O:18].[Na+].[Na+].NO.Cl.OS(O)(=O)=O>O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:6](=[CH:8][CH:9]=1)[NH:7][C:11](=[O:18])[C:12]2=[O:14])[CH3:2]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 2707Chloral HydrateHCID 115044-EthylanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5834875-ethyl-2,3-dihydro-1H-indole-2,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The title compound is prepared starting from 30 g (0.248 mol) of p-ethylaniline (Fluka, Buchs, Switzerland), 54 g (0.326 mol) chloral hydrate, and 750 g sodium sulfate in 800 ml water followed by the addition of 60 g (0.863 mol) NH2OH—HCl in water. By treating the intermediate with conc. H2SO4, the final product is obtained. (For the procedure, see Ng. Ph. Buu-Hoi et. al. in J. Chem. Soc., 4867 (1952)). The crude compound is used in the next step without further purification. Only a small sample is crystallized from methanol for analytical purposes. mp: 135-137° C. (Lit.: 135° C.); MS: 174 (M+−+1); HPLC: tret=8.74 min (Grad 1).

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-269e82a13c04485ca3e04167909dcd83
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

Loading…