2-Naphthylamine → HCID 86607482, 화합물

HRID 14430

반응식

HRID 14430 반응식
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]

참가 물질

3

반응물 2

HCID 70572-NaphthylamineHCID 71446589Cinnamyl carbonate

생성물 1

HCID 86607482HCID 86607482, 화합물수율 89.3%

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8486f8fa9c3b4c1bad74f352f03d9cd7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

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