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

HRID 2423316

반응식

HRID 2423316 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-16d0c3b2ffd34074ae81e23fc3d08fa6
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960567B2

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