1,4-Dioxane → HCID 9905094, compound

HRID 2308235Notes

Reaction equation

HRID 2308235 reaction equation
[CH3:1][CH:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[CH:8]=2)[NH:3]1.O1CCOCC1.[ClH:28].O1CCOCC1>CCOCC>[ClH:28].[CH3:1][CH:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 9851526HCID 9851526, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 9905094HCID 9905094, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,3-trimethyl-5-(3-nitro-phenyl)-2,3-dihydro-1H-indole (0.8 g, 2.79 mmol) in 20 mL of 1:1 ether:dioxane at room temperature was treated with 1.5 mL of a 4 M HCl/dioxane solution. The resulting solid was isolated by filtration and washed with hexane to afford the title compound (0.81 g, 90%) as a tan solid: mp. 240-241° C.; 1H-NMR (CDCl3) δ 1.37 (s, 3H), 1.51 (s, 3H), 4.01 (d, J=6.5 Hz, 1H) 7.51 (s, 1H), 7.59 (d, J=7.3 Hz, 1H), 7.7 (dd, J=7.9, 7.9 Hz, 1H), 7.8 (d, J=7.9, Hz, 1H), 7.89 (d, J=7.7 Hz, 1H), 8.3 (dd, J=7.9, 1.8 Hz, 1H), 8.42 (s, 1H), 11.9 (br s. 2H); 13C-NMR (CDCl3) δ ; MS (EI) m/z 283 (M+H)+.

Workup

  1. customThe resulting solid was isolated by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-b8f5296353ba44569510d05180cb2fe6
Source dataset
uspto-grants-2004_12
Patent number
US06835744B2

Reaction notes

Loading…