Hydrochloric Acid → 2-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

HRID 2423316

反応式

HRID 2423316 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[OH:29].Cl>CS(C)=O.CCOC(C)=O.O>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[O:29][C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1738Homovanillic AcidHCID 10796Cesium carbonateHCID 40708006-Chloro-5-nitroquinoline

生成物 1

HCID 598648342-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

Cs2CO3 (15.5 g, 47.5 mmol) was added to (24.1) (3 g, 14.4 mmol) and 3-methoxy-4-hydroxyphenylacetic acid (2.63 g, 14.4 mmol) in DMSO (30 mL) at room temperature. The mixture was then stirred at 80° C. for 4 h. After cooling, the reaction mixture was treated with water (50 mL), 3N HCl (35 mL) and EtOAc (100 mL). The product was insoluble in EtOAc, but stayed in the organic layer. So the organic layer was washed with water 4 times to get rid of all the salts, and the organic layer was separated, concentrated and dried under vacuum to afford 24.2. MS ESI (pos.) m/z: 355.1 (M+H). 1H NMR (DMSO-d6) δ 8.99 (dd, 1H); 8.24 (m, 2H); 7.77 (dd, 1H); 7.29 (d, 1H); 7.21 (d, 1H); 7.18 (d, 1H); 6.96 (dd, 1H); 3.73 (s, 3H); 3.65 (s, 2H).

後処理

  1. temperatureAfter cooling
  2. washSo the organic layer was washed with water 4 times
  3. customto get rid of all the salts
  4. customthe organic layer was separated
  5. concentrationconcentrated
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-16d0c3b2ffd34074ae81e23fc3d08fa6
出典データセット
uspto-grants-2011_06
特許番号
US07960567B2

関連ノート

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