Morpholine → 2-Methyl-4-(morpholin-4-yl)-7-nitro-2,3-dihydro-1H-isoindol-1-one

HRID 1948019Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][N:5]1[CH2:4][C:3]2[C:7](=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=2[N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:6]1=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-Bromo-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (100.0 mg, 0.3689 mmol), morpholine (321.7 uL, 3.689 mmol), DIPEA (642.6 uL, 3.689 mmol) in DMF (4 mL) were mixed in sealed tube under an atmosphere of argon and heated at 90° C. for 4 days. The crude material was purified by MDP directly under basic conditions the desired product. MS (ES+): m/z 278.24 (100) [MH+]; HPLC: tR=0.81 min (UPLC, analytical).

Workup

additionwere mixed in sealed tube under an atmosphere of argon
customThe crude material was purified by MDP directly under basic conditions the desired product

Sources & evidence

ORD record: ord-8f6ebd7bffae4dcc98734c3c217dbc80
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

Loading…