2-Naphthylamine → HCID 86607482、化合物

HRID 14430

反応式

HRID 14430 の反応式
C(=O)([O-])O[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[NH2:24]>>[C:4]([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH:24][C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=1)#[CH:3]

参加物

3

反応物 2

HCID 70572-NaphthylamineHCID 71446589Cinnamyl carbonate

生成物 1

HCID 86607482HCID 86607482、化合物収率 89.3%

実験手順

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and 2-napthylamine (0.170 g, 1.18 mmol). The reaction was conducted at room temperature for 16 h. 1H NMR analysis of the crude reaction mixture indicated the ratio of regioisomers to be 99/1. The mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes) to give the title compound (0.225 g, 89%). [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.53 (d, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.31-7.11 (m, 6H), 7.06 (t, J=7.6 Hz, 1H), 6.76 (dd, J=9.0, 2.2 Hz, 1H), 6.64 (d, J=2.0 Hz, 1H), 5.95 (ddd, J=17.2, 10.4, 6.0 Hz, 1H), 5.20 (d, J=17.6 Hz, 1H), 5.13 (d, J=9.6 Hz, 1H), 4.94 (d, J=5.6 Hz, 1H), 4.06 (br s, 1H). 13C NMR (100.59 MHz, CDCl3) δ 144.65, 141.52, 138.63, 134.90, 128.74, 128.73, 127.53, 127.48, 127.45, 127.14, 126.18, 125.99, 122.04, 118.02, 116.16, 105.82, 60.18. Anal. Calcd for C19H17N: C, 87.99; H, 6.61; N, 5.40. Found: C, 88.16; H, 6.58; N, 5.41.

後処理

  1. custom1H NMR analysis of the crude reaction mixture
  2. customThe mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8486f8fa9c3b4c1bad74f352f03d9cd7
出典データセット
uspto-grants-2010_06
特許番号
US07732365B2

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