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

HRID 1502729ノート

反応式

HRID 1502729 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c77b3de7d58d412c98284553c88de0d1
出典データセット
uspto-grants-2015_12
特許番号
US09210927B2

反応ノート

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