Triethylamine → HCID 178515071、化合物

HRID 323628

反応式

HRID 323628 の反応式
CO[C:3]([C:5]1[C:14]([C:15]([O:17]C)=O)=[C:13]([OH:19])[C:12]2[C:7](=[CH:8][C:9]([Cl:20])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].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:20][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[O:19])[C:14]3[C:15]([OH:17])=[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:3](=[O:4])[C:5]=3[NH:6][C:7]=2[CH:8]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 178418477HCID 178418477、化合物

生成物 1

HCID 178515071HCID 178515071、化合物収率 79.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.00 g, 6.80 mM) and 1-naphthylhydrazine 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 with hydrochloric acid (3×500 mL, 1N). The washed solution was diluted with ether (250 mL) to give a tan suspension. The solids were collected to give the 1-naphthylhydrazine 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 (1.44 g, 54%) as a tan powder, mp 368° C. (decomp.); MS(CI): 390 (M+H).

後処理

  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 with hydrochloric 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

出典と根拠

ORDレコード
ord-eb02e63b032941dabac9cdaf87e4cebf
出典データセット
uspto-grants-2001_04
特許番号
US06214826B1

関連ノート

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