4-(Bromomethyl)-1-naphthaldehyde → 4-((1,3-Dioxoisoindolin-2-yl)methyl)-1-naphthaldehyde

HRID 587723Notes

Reaction equation

HRID 587723 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>CN(C=O)C.O>[O:20]=[C:18]1[C:17]2[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:25])[N:19]1[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 109119034-(Bromomethyl)-1-naphthaldehydeHCID 24194345Phthalimide potassium salt

Product 1

HCID 866751874-((1,3-Dioxoisoindolin-2-yl)methyl)-1-naphthaldehydeYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-(bromomethyl)-1-naphthaldehyde (7 g, 28 mmol) in DMF (100 mL) was added potassium phthalimide (7.3 g, 39.5 mmol), and the mixture was heated at 85° C. for 2 h. The reaction mixture was cooled to ambient temperature and diluted with water (100 mL). The obtained solid was separated by filtration and dried under vacuum to afford the title compound as a white solid (8.8 g, 98%): mp 190-192° C.; 1H NMR (400 MHz, CDCl3) δ 10.39 (s, 1H), 9.25 (m, 1H), 8.41 (m, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.95 (m, 4H), 7.80 (m, 4H), 7.61 (m, 4H), 5.39 (s, 2H); ESIMS m/z 316.09 ([M+H]+); IR (thin film) 1708 cm−1.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe obtained solid was separated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3f8ccc92d2714f92a68944ca35c8dbf0
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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