Diisopropylethylamine → N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

HRID 2178424ノート

反応式

HRID 2178424 の反応式
F[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].Cl.[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=3)=[CH:4][C:3]=2[N+:20]([O-:22])=[O:21])=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27240964-Bromobenzylamine hydrochlorideHCID 904169762-((4-Fluoro-3-nitrophenoxy)methyl)quinoline

生成物 1

HCID 90414040N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline収率 113.1%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

To a 250 mL round-bottomed flask were added a stir bar, 2-((4-fluoro-3-nitrophenoxy)methyl)quinoline (15.0 g, 40 mmol) and 4-bromobenzyl amine hydrochloride (11 g, 50 mmol), DMA (130 mL), and DIPEA (22 mL, 125 mmol). The resulting mixture was heated to 100° C. After 24 h, the mixture was cooled and concentrated to dryness. The residue was triturated with IPA (200 mL) and the orange solid was collected by vacuum filtration. The collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL) to afford the title compound (21 g, 84%). MS (ESI): mass calcd. for C23H18BrN3O3, 463.05; m/z found 464.1 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.34-8.27 (m, 1H), 8.21 (d, J=8.4, 1H), 8.12-8.06 (m, 1H), 7.87-7.81 (m, 2H), 7.75 (ddd, J=8.4, 6.9, 1.4, 1H), 7.63 (d, J=8.5, 1H), 7.58-7.53 (m, 1H), 7.49-7.46 (m, 2H), 7.25-7.18 (m, 3H), 6.71 (d, J=9.4, 1H), 5.34 (s, 2H), 4.49 (d, J=5.8, 2H).

後処理

  1. additionTo a 250 mL round-bottomed flask were added a stir bar
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated to dryness
  4. customThe residue was triturated with IPA (200 mL)
  5. filtrationthe orange solid was collected by vacuum filtration
  6. washThe collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL)

出典と根拠

ORDレコード
ord-0a0f55cd9ee34d0abe13cc3aff3b34d6
出典データセット
uspto-grants-2015_06
特許番号
US09067917B2

反応ノート

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