4-Isopropylaniline → HCID 57429433, compound

HRID 1640023Notes

Reaction equation

HRID 1640023 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:4]=1[C:5]([O:7]CC)=O.[CH:17]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(N(CC)C(C)C)(C)C>C(O)C>[CH:17]([C:20]1[CH:26]=[CH:25][C:23]([N:24]2[CH2:2][C:3]3[C:4](=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=3)[C:5]2=[O:7])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 74644-IsopropylanilineHCID 81531DiisopropylethylamineHCID 18510925HCID 18510925, compound

Product 1

HCID 57429433HCID 57429433, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-(bromomethyl)-5-nitrobenzoate (1.88 g, 6.52 mmol), 4-isopropylaniline (1.11 mL, 7.83 mmol) and N,N-diisopropylethylamine (1.36 mL, 7.83 mmol) in ethanol (75 mL) was heated in a sealed tube at 110° C. overnight. After this time, the mixture was cooled to room temperature and the solid collected by filtration to afford 2-(4-isopropylphenyl)-6-nitroisoindolin-1-one (1.45 g, 75%) as a yellow solid: mp 225-227° C.; 1H NMR (300 MHz, CDCl3) δ 8.77 (d, J=2.0 Hz, 1H) 8.48 (dd, J=8.3, 2.1 Hz, 1H), 7.76-7.69 (m, 3H), 7.32 (d, J=8.6 Hz, 2H), 2.94 (sept, J=6.9 Hz, 1H), 1.28 (d, J=6.9 Hz, 6H); ESI MS m/z 297 [M+H]+.

Workup

  1. temperatureAfter this time, the mixture was cooled to room temperature
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-02ab4ca4a8034b3297fc409504666fe7
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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