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

HRID 511449Notes

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-5c40a8e69fe440a9bab904050df8f8ff
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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