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

HRID 260760
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HRID 260760 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 3871957H-Naphtho(1,2,3-ij)(2,7)naphthyridin-7-one2회HCID 99048014-Bromosampangine

생성물 2

HCID 99048014-Bromosampangine수율 64%HCID 103161514-Bromo-5-ethoxysampangine수율 1%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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 NaHCO3Solution (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) δ7.72 (ddd, 1 H, J=7.9, 7.9, 1.4 Hz), 7.86 (ddd, 1 H, J=7.9, 7.9, 1.4 Hz), 7.96 (d, 1 H, J=5.9 Hz), 8.46 (dd, 1 H, J=7.9, 1.4 Hz), 8.85 (dd, 1 H, J=7.9, 1.4 Hz), 8.99 (d, 1 H, 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) δ1.56 (t, 3 H, J=7.1 Hz), 4.79 (q, 2 H, J=7.1 Hz), 7.67 (ddd, 1 H, J=7.3, 7.3, 1.4 Hz), 7.79 (ddd, 1 H, J=7.3, 7.3, 1.4, Hz), 7.82 (d, 1 H, J=6.1 Hz), 8.36 (dd, 1 H, J=7.3, 1.4 Hz), 8.72 (d, 1 H, J=6.1 Hz), 8.75 (dd, 1 H, 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.

후처리

  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 NaHCO3Solution (2×250 mL)
  6. dry with materialThe organic layer was dried (K2CO3)
  7. concentrationconcentrated to dryness
  8. washwhile eluting with CHCl3

출처 및 근거

ORD 기록
ord-c5efb14e929b4f609a85a7b8bd558e71
출처 데이터셋
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05530004

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