Hydrochloric Acid → 2-(4-tert-butyl-phenyl)-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 133111Notes

Reaction equation

HRID 133111 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=1.Cl>O1CCOCC1>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([N:15]2[CH2:14][CH2:13][C:5]3[C:4](=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:2])=[CH:17][CH:18]=1)([CH3:23])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 691591522-[2-(4-Tert-butyl-phenylamino)-ethyl]-6-nitro-benzoic acid methyl ester

Product 1

HCID 691594242-(4-tert-butyl-phenyl)-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the amine (Step C, 0.41 g, 1.2 mmol), conc. HCl (0.1 mL), and dioxane (4 mL) was heated in a microwave at 200° C. for 5 min. The mixture was concentrated in vacuo to give the crude compound as a red oil. Purification by silica flash chromatography (0-25% EtOAc:hexane) gave the desired compound as a yellow oil. MS m/e 325 (M+H)+. Calc'd for C19H20N2O3-324.37.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give the crude compound as a red oil
  3. customPurification by silica flash chromatography (0-25% EtOAc:hexane)

Sources & evidence

ORD record
ord-c2b21c42628d4085a142aeb110d448a8
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

Loading…