1,2-Dibromopentane → 2-(5-Bromopentyl)benzo[de]isoquinoline-1,3-dione

HRID 2172659Notes

Reaction equation

HRID 2172659 reaction equation
[C:1]1(=[O:15])[C:10]2[C:5]3[C:6](=[CH:11][CH:12]=[CH:13][C:4]=3[C:3](=[O:14])[NH:2]1)[CH:7]=[CH:8][CH:9]=2.[Br:16][CH2:17][CH:18](Br)[CH2:19][CH2:20][CH3:21]>>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:2]1[C:3](=[O:14])[C:4]2[CH:13]=[CH:12][CH:11]=[C:6]3[C:5]=2[C:10](=[CH:9][CH:8]=[CH:7]3)[C:1]1=[O:15]

Participants

3

Reactant 2

HCID 295711,2-DibromopentaneHCID 66491Naphthalimide

Product 1

HCID 166387912-(5-Bromopentyl)benzo[de]isoquinoline-1,3-dione

Procedure

This compound was prepared according to GP-1 using benzo[de]isoquinoline-1,3-dione (1) and 1,2 dibromopentane (2c) The crude product was purified by flash column chromatography using EtOAc-hexane to give 3c. 1H NMR (500 MHz, CDCl3) δ 8.63 (d, J=7.5 Hz 2H), 8.24 (d, J=8.0 Hz, 2H), 7.78 (t, J=7.5 Hz, 2H), 4.22 (t, J=7.0, 2H), 3.45 (t, J=7.0 Hz, 2H), 2.01-1.94 (m, 2H), 1.84-1.78 (m, 2H), 1.64-1.57 (m, 2H), MS (ES+) m/z 368 (M+Na)+.

Workup

  1. customThis compound was prepared
  2. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-bf905848b0cc463bb87e41e620b559bf
Source dataset
uspto-grants-2015_06
Patent number
US09056835B2

Reaction notes

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