Triethylamine → 2-Ethyl-2,3-dihydro-5-nitro-1H-isoindole

HRID 1669179Notes

Reaction equation

HRID 1669179 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12]Br.Cl.[CH2:15]([NH2:17])[CH3:16].CCN(CC)CC>CN(C=O)C>[CH2:15]([N:17]1[CH2:12][C:4]2[C:3](=[CH:8][CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=2)[CH2:2]1)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 108523601,2-Bis(bromomethyl)-4-nitrobenzene

Product 1

HCID 251398882-Ethyl-2,3-dihydro-5-nitro-1H-isoindoleYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of dibromide 118 (9.27 g, 30.0 mmol), ethylamine hydrochloride (2.45 g, 30.0 mmol) and Et3N (21 mL, 150 mmol) in DMF (100 mL) was stirred at 20° C. for 90 min. The mixture was partitioned between EtOAc and aqueous Na2CO3 solution. The organic fraction was washed with water, dried and the solvent evaporated to give isoindole 245 (3.21 g, 56%) as a dark oil: 1H NMR δ 8.11 (dd, J=8.1, 2.1 Hz, 1H, H-6), 8.05 (d, J=2.1 Hz, 1H, H-4), 7.34 (d, J=8.1 Hz, 1H, H-7), 3.99 (s, 4H, H-1, H-3), 2.82 (q, J=7.2 Hz, 2H, CH2), 1.22 (t, J=7.2 Hz, 3H, CH3); HRMS (FAB+) calcd for C10H13N2O2 (MH+) m/z 193.0977, found 193.0983.

Workup

  1. customThe mixture was partitioned between EtOAc and aqueous Na2CO3 solution
  2. washThe organic fraction was washed with water
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-794cad4c0bf3458d9636e77d3b077a84
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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