Potassium Carbonate → 6-((3-(4-chlorobenzyl)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023194ノート

反応式

HRID 1023194 の反応式
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14]([O:16]CC)=O)[CH:8]=2)[NH:3]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=[N:29]O)[NH2:28])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]2[N:28]=[C:14]([CH2:13][O:12][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:11][CH2:10]4)[O:16][N:29]=2)=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2493452-(4-chlorophenyl)-N'-hydroxyethanimidamideHCID 12821879Ethyl 2-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetate

生成物 1

HCID 866804336-((3-(4-chlorobenzyl)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one収率 27%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a stirred solution of ethyl 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetate (0.1 g, 0.4 mmol) in dry toluene (2 mL), 2-(4-chlorophenyl)-N′-hydroxyacetimidamide (0.073 g, 0.4 mmol) and potassium carbonate (0.1 g, 8 mmol) were added and heated to 110° C. in a microwave oven for 30 min. Solvent was removed under vacuum. Water (5 mL) was added to the residue, and the solid which formed was filtered, dried, and recrystallized using a mixture of ACN/Ethanol to afford 6-((3-(4-chlorobenzyl)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one as an off-white solid (40 mg, 27%). 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=7.60 Hz, 2H), 4.14 (s, 2H), 5.39 (s, 2H), 6.78-6.83 (m, 2H), 6.89 (d, J=2.40 Hz, 1H), 7.33 (d, J=8.40 Hz, 2H), 7.40 (d, J=8.40 Hz, 2H), 9.95 (s, 1H). LCMS: RT 1.85 min. LCMS (ES-API), m/z 370.0 (M+H).

後処理

  1. customSolvent was removed under vacuum
  2. additionWater (5 mL) was added to the residue
  3. customthe solid which formed
  4. filtrationwas filtered
  5. customdried
  6. customrecrystallized
  7. additiona mixture of ACN/Ethanol

出典と根拠

ORDレコード
ord-bfe12770fcdd447e992131d79c7e68c1
出典データセット
uspto-grants-2014_05
特許番号
US08722670B2

反応ノート

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