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3-Aminobenzoic Acid → 5-(3-Aminobenzoyloxymethyl)-6-(4-fluoro-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909323
ノート
印刷プレビュー

反応式

HRID 909323 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][OH:22])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:23][CH3:24])[CH:3]=1.[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](O)=[O:30].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([O:22][CH2:21][C:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[O:23][CH3:24])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:20])=[CH:12][C:13]([CH3:19])([CH3:18])[NH:14]2)=[O:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 74193-Aminobenzoic AcidHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 580268476-(4-Fluoro-2-methoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline

生成物 1

HCID 580268295-(3-Aminobenzoyloxymethyl)-6-(4-fluoro-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline収率 42%

試薬・触媒・溶媒

3
HCID 241Benzene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

6-(4-Fluoro-2-methoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 4-3, 49.7 mg, 0.15 mmol), 3-aminobenzoic acid (49.0 mg, 0.35 mmol), tri-n-butylphosphine (87.0 μL, 0.35 mmol), and 1,1′-(azodicarbonyl)dipiperidine (89.4 mg, 0.35 mmol) were dissolved in anhydrous benzene (2 mL), and then the mixture was stirred under argon atmosphere at room temperature overnight. Hexane (3 mL)-ethyl acetate (3 mL) were added to the reaction mixture, and unsoluble materials were filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (28.0 mg) as a colorless amorphous product. (Yield 42%)

後処理

  1. filtrationwere filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-410894fb5efa4c4c8ad33ace603970b5
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017775B2

反応ノート

読み込み中…

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