Triethylamine → HCID 178515071, 화합물

HRID 1600042

반응식

HRID 1600042 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18]C)=O)[C:8]([C:12]([O:14]C)=O)=[N:9]2)=[CH:4][CH:3]=1.Cl.[C:22]1([NH:32][NH2:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:16]([OH:18])=[N:33][N:32]([C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24][CH:23]=4)[C:12](=[O:14])[C:8]=3[NH:9][C:10]=2[CH:11]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 178418477HCID 178418477, 화합물

생성물 1

HCID 178515071HCID 178515071, 화합물수율 54.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.00 g, 6.80 mM) and 1-naphthyl hydrazine hydrochloride (9.26 g, 47.6 mM) in ethanol (72 mL) was added triethylamine (7.60 mL) to give a brown solution. After refluxing for 4 days, the solution was cooled to room temperature and diluted with ethyl acetate (0.35 L) to give a tan suspension. This suspension was filtered to remove the solids which were discarded. The filtrate was then poured into ethyl acetate (500 mL) which was washed withhydrochloric acid (3×500 mL, 1N). The washed solution was diluted with ether (250 mL) to give a tan suspension. The solids were collected togive the 1-naphthyl hydrazine salt of the title compound as a tan powder (2.09 g). This material was refluxed in glacial acetic acid (50 mL) for 2 hours, cooled to room temperature and filtered. The collected solids were washed with glacial acetic acid and ether to give the title compound (1.44g, 54%) as a tan powder, mp 368° C. (decomp.); MS(CI): 390 (M+H). Analysis for 21H12ClN3O3·0.30 CH3CO2H: Calculated: C, 63.60; H, 3.26; N, 10.30 Found: C, 63.90; H, 3.43; N, 9.97 1H NMR 9.06 (s, 1H exchangeable), 8.27-8.22 (m, 2H), 7.92-7.88 (m, 2H), 7.63-7.52 (m, 3H), 7.41 (d, J=8.17 Hz, 1H), 7.27 (t, J=7.86 Hz, 1H), 6.80 (d, J=7.86 Hz, 1H).

후처리

  1. customto give a brown solution
  2. temperatureAfter refluxing for 4 days
  3. customto give a tan suspension
  4. filtrationThis suspension was filtered
  5. customto remove the solids which
  6. additionThe filtrate was then poured into ethyl acetate (500 mL) which
  7. washwas washed withhydrochloric acid (3×500 mL, 1N)
  8. additionThe washed solution was diluted with ether (250 mL)
  9. customto give a tan suspension
  10. customThe solids were collected togive the 1-naphthyl hydrazine salt of the title compound as a tan powder (2.09 g)
  11. temperatureThis material was refluxed in glacial acetic acid (50 mL) for 2 hours
  12. temperaturecooled to room temperature
  13. filtrationfiltered
  14. washThe collected solids were washed with glacial acetic acid and ether

출처 및 근거

ORD 기록
ord-45aaeff404194f39b3c7fe7baaf97878
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744471

연결된 노트

불러오는 중…