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

HRID 1504683Notes

Reaction equation

HRID 1504683 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 H2O (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-f84377bf66354878ba9ad76d9440f8f2
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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