Water → 1-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 250408

반응식

HRID 250408 반응식
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:22])=O.O>C(#N)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:22])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 1784508431,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester

생성물 1

HCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester수율 3.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

2 g (7.7 mmol) of 1,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester (from Example D-20 b) dissolved in 100 ml of acetonitrile. 15.4 g (53.6 mmol) of phosphorous oxybromide added to solution and mixture stirred at 80° C. for 64 h. 100 ml of water was added to mixture, and mixture was removed from heat. Mixture was partitioned between ethyl acetate and water. Two phases were separated and the aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with brine, dried over magnesium sulfate, filtered, and evaporated. Residue was purified by silica gel flash chromatography to give 0.1 g (0.3 mmol) of product. 1H NMR (200 MHz, CDCl3) δ 11.89 (s, 1H), 8.41 (m, 1H), 8.25 (m, 1H), 7.84 (m, 2H), 4.49 (t, J=7.0 Hz, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 1.00 (t, J=7.2 Hz, 3H).

후처리

  1. customwas removed
  2. temperaturefrom heat
  3. customMixture was partitioned between ethyl acetate and water
  4. customTwo phases were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customResidue was purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-10cff72e97344bb4b8e20239bd6c170d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863292B2

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