Triethylamine → HCID 59276626, compound

HRID 2070874Notes

Reaction equation

HRID 2070874 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-])=O)[CH:12]=2)[C:7]1=[O:18].BrCC1C=C([N+]([O-])=O)C=CC=1C(OC)=O.COC1C=C(OC)C=CC=1CN.C(N(CC)CC)C>CO.C(OCC)(=O)C.CCCCCC>[NH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:18])[N:6]([CH2:5][C:4]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:3]=1[O:2][CH3:1])[CH2:14]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoateHCID 67293384HCID 67293384, compound

Product 1

HCID 59276626HCID 59276626, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

2-(2,4-Dimethoxybenzyl)-5-nitroisoindolin-1-one. A mixture of methyl 2-(bromomethyl)-4-nitrobenzoate (2.5 g, 9.12 mmol), (2,4-dimethoxyphenyl)methanamine (1.525 g, 9.12 mmol), triethylamine (3.81 mL, 27.4 mmol) in methanol (25 mL) was refluxed for 16 h. The mixture was diluted with ethyl acetate, washed with dilute hydrochloric acid and brine, dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to dryness. Flash chromatography (30-50% ethyl acetate in hexane) gave the desired product as a yellow solid (2.5 g, 7.68 mmol, 84% yield). MS (ESI) m/z 329.9 [M+1]+.

Workup

  1. temperaturewas refluxed for 16 h
  2. washwashed with dilute hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator to dryness

Sources & evidence

ORD record
ord-0bb910f189f44b9a8551445dae86a937
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

Loading…