Potassium Bromide → 5-(2-Bromo-ethyl)-5, 6-dihydro-phenanthridine

HRID 550856

反応式

HRID 550856 の反応式
CN(C=O)C.CCO[CH2:9][CH3:10].[K+].[Br-:12].[Br-].BrCC[C:17]1[C:30]2[C:21](=[NH+:22][CH:23]=[C:24]3[C:29]=2[CH:28]=[CH:27][CH:26]=[CH:25]3)[CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[Br:12][CH2:24][CH2:23][N:22]1[CH2:9][C:10]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]1=2

参加物

5

反応物 3

HCID 253877Potassium BromideHCID 19966313DMF etherHCID 671881532-Bromo-ethyl-phenanthridinium bromide

生成物 1

HCID 111969725-(2-Bromo-ethyl)-5, 6-dihydro-phenanthridine収率 50%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

During the preparation of 6a, the mother liquor from the DMF/ether (25:75) solution was kept and washed thoroughly 4 times with 40 ml of water. The organic layer was then washed with brine and dried over MgSO4. The solvent was evaporated down to a dark residue. Column chromatography (Silica, DCM as elutant) afforded 5 (140 mg; 0.485 mmol) as a beige powder in a 50% yield. Rf=0.75 in 100% ethyl acetate; mp: 99-100° C.; 1H NMR (CDCl3, 400 MHz): δ 7.64 (d, 1H, J=7.60 Hz), 7.60 (d, 1H, J=7.60 Hz), 7.22 (t, 1H, J=7.60 Hz), 7.13 (t, 2H, J=7.60 Hz), 7.01 (d, 1H, J=7.60 Hz), 6.77 (t, 1H, J=7.60 Hz), 6.62 (d, 1H, J=7.60 Hz), 4.27 (s, 2H), 3.64 (t, 2H, J=7.80 Hz), 3.44 (t, 2H, J=7.80 Hz); 13C NMR (CDCl3, 100 MHz): δ 145.02 (C), 132.71 (C), 132.19 (C), 129.68 (CH), 128.55 (CH), 128.22 (CH), 125.96 (CH), 124.44 (CH), 124.22 (C), 123.59 (CH), 119.19 (CH), 112.51 (CH), 53.38 (CH2), 53.26 (CH2), 27.78 (CH2); IR (KBr, cm−1): 3429 (s), 2924 (w), 1716 (w), 1628 (s), 1601 (s), 1525 (w), 1493 (s), 1442 (s), 1340 (m), 1290 (m), 1269 (s), 1196 (s), 1022 (m), 758 (s), 725 (m), 615 (m) MS (FAB): 289 (M+H) (100), 222.1 (7), 194.1 (35), 180.1 (22), 166.1 (6), 152.1 (4), 107.2 (2), 85.7 (1), 58.1 (7); Anal. Calcd for C15H14NBr: C, 62.51; H, 4.89; N, 4.86. Found: C, 62.30; H, 4.96; N, 4.75.

後処理

  1. washwashed thoroughly 4 times with 40 ml of water
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated down to a dark residue
  5. customColumn chromatography (Silica, DCM as elutant) afforded 5 (140 mg; 0.485 mmol) as a beige powder in a 50% yield

出典と根拠

ORDレコード
ord-9aa5a46564204afabee6e8f062b4d207
出典データセット
uspto-grants-2011_05
特許番号
US07947703B2

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