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7H-Naphtho(1,2,3-ij)(2,7)naphthyridin-7-one → 4-Bromosampangine

HRID 483833
ノート
印刷プレビュー

反応式

HRID 483833 の反応式
C1C=CC2[C:17](=[O:18])[C:16]3C4C(C=CN=3)=CC=NC=4C=2C=1.[Br:19][C:20]1[C:29]2[C:24]3=[C:25]([C:30]4[C:35]([C:36](=[O:37])[C:23]3=[N:22][CH:21]=1)=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:26]=[CH:27][CH:28]=2.C1C=C[NH+]=CC=1.Br[Br-]Br>C(Cl)(Cl)Cl>[CH:32]1[CH:31]=[C:30]2[C:25]3[C:24]4[C:23]([C:36](=[O:37])[C:35]2=[CH:34][CH:33]=1)=[N:22][CH:21]=[C:20]([Br:19])[C:29]=4[CH:28]=[CH:27][N:26]=3.[CH3:16][CH2:17][O:18][C:21]1[N:22]=[C:23]2[C:24]3[C:25]([C:30]4[C:35]([C:36]2=[O:37])=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:26][CH:27]=[CH:28][C:29]=3[C:20]=1[Br:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3871957H-Naphtho(1,2,3-ij)(2,7)naphthyridin-7-one2 回HCID 99048014-Bromosampangine

生成物 2

HCID 99048014-Bromosampangine収率 64%HCID 103161514-Bromo-5-ethoxysampangine収率 1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Electrophilic Bromination of Sampangine: Preparation of 4-Bromo-7H-naphtho[1,2,3-ij] [2,7]naphthyridin-7-one [4-Bromosampangine, 5] and 4-Bromo-5-ethoxy-7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-one[4-Bromo-5-ethoxysampangine, 20]. A mixture of pyridinium bromide perbromide (4.80 g, 15.0 mmol) and sampangine (2.32 g, 10.0 mmol) in CHCl3 (100 mL) was heated at reflux for 24 h. After cooling, the mixture was poured into a separatory funnel and washed with saturated aqueous NaHCO3 solution (2×250 mL). The organic layer was dried (K2CO3) and concentrated to dryness. The residual solids were subjected to flash silica gel chromatography while eluting with CHCl3 to give pure 4-bromosampangine (5) (2.00 g, 64%) and 4-bromo-5-ethoxysampangine (20) (0.05 g, 1%). An analytical sample of 20 was obtained by crystallization from CHCl3. Compound 5: mp 244°-246° C.; IR (KBr) 1670, 1590, 1400, 1320, 1310, 1275, 1230, 980, 790, 755, 720 cm-1 ; 1H NMR (CDCl3) δ 7.72 (ddd, 1H, J=7.9, 7.9, 1.4 Hz), 7.86 (ddd, 1H, J=7.9, 7.9, 1.4 Hz), 7.96 (d, 1H, J=5.9 Hz), 8.46 (dd, 1H, J=7.9, 1.4 Hz), 8.85 (dd, 1H, J=7.9, 1.4 Hz), 8.99 (d, 1H, J=5.9 Hz), 9.28 (s,1H); 13C NMR (CDCl3) 118.3 (1), 120.5 (0), 123.7 (0), 125.8 (1), 128.7 (1), 131.8 (1), 132.3 (0), 135.0 (1), 135.1 (0), 138.6 (0), 146.7 (0), 148.6 (1), 150.2 (1), 151.7 (0), 181.6 (0) ppm; Anal. (exact mass, HREIMS) calcd for C15H7BrN2O m/e 309.9741, found 309.9747; Anal. calcd for C15H7BrN2O: C 57.90, H 2.27, N 9.00; found C 57.70, H 2.27, N 9.26. Compound 20: mp 200°-201° C.; IR (KBr) 1670, 1592, 1570, 1430, 1382, 1365, 1330, 1270, 1212, 1080, 1070, 1042, 980, 845, 762, 755, 720, 710, 635 cm-1 ; 1H NMR (CDCl3) δ 1.56 (t, 3H, J=7.1 Hz), 4.79 (q, 2H, J=7.1 Hz), 7.67 (ddd, 1H, J=7.3, 7.3, 1.4 Hz), 7.79 (ddd, 1H, J=7.3, 7.3, 1.4 Hz), 7.82 (d, 1H, J=6.1 Hz), 8.36 (dd, 1H, J=7.3, 1.4 Hz), 8.72 (d, 1H, J=6.1 Hz), 8.75 (dd, 1H, J=7.3, 1.4 Hz); 13C NMR (CDCl3) 14.6 (3), 64.7 (2), 107.4 (0), 117.5 (0), 117.8 (1), 125.5 (1), 128.2 (1), 131.4 (1), 132.2 (0), 134.5 (1), 135.0 (0), 140.9 (0), 144.6 (0), 147.2 (1), 151.7 (0), 159.9 (0), 181.4 (0) ppm; Anal. calcd for C17H11BrN2O: C 57.48, H 3.12, N 7.88; found C 57.09, H 3.37, N 7.75.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. temperatureAfter cooling
  4. additionthe mixture was poured into a separatory funnel
  5. washwashed with saturated aqueous NaHCO3 solution (2×250 mL)
  6. dry with materialThe organic layer was dried (K2CO3)
  7. concentrationconcentrated to dryness
  8. washwhile eluting with CHCl3

出典と根拠

ORDレコード
ord-7bacae8099d443b2ba16d4de394f5c91
出典データセット
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05227383

反応ノート

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