Benzyl Bromide → 1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 394459ノート

反応式

HRID 394459 の反応式
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13].CC(C)([O-])C.[K+].C1COCC1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([N:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 127895324H-Imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 97952141-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I, J. Heterocyclic Chem.,19, 837-49 (1982), 1.0 g, 5.8 mmol) in DMF (10 ml) is cooled to 0° and treated with potassium t-butoxide in THF (1.98 M, 3.2 ml, 6.3 mmol) maintaining the reaction temperature at 0°. The resulting mixture is stirred at 0° for 10 minutes. Benzyl bromide (0.73 ml, 6.1 mmol) is then added while maintaining the reaction temperature at 0°. After 1 hour, the mixture is partitioned with methyl t-butyl ether (MTBE) from water followed by several water washes. The MTBE phase is concentrated under reduced pressure. The concentrate is cooled to 0°, filtered and washed two times with 0° MTBE. The product is dried at 50° under reduced pressure with a nitrogen purge to give the title compound, CMR (CDCl3, 100 MHz) 153.78, 136.44, 128.69, 127.67, 127.60, 126.73, 125.86, 122.90, 122.78, 121.28, 116.92, 116.17, 108.36, 44.95 and 42.37 δ.

後処理

  1. temperatureis cooled to 0°
  2. temperaturemaintaining the reaction temperature at 0°
  3. temperaturewhile maintaining the reaction temperature at 0°
  4. waitAfter 1 hour
  5. customthe mixture is partitioned with methyl t-butyl ether (MTBE) from water
  6. concentrationThe MTBE phase is concentrated under reduced pressure
  7. temperatureThe concentrate is cooled to 0°
  8. filtrationfiltered
  9. washwashed two times with 0° MTBE
  10. customThe product is dried at 50° under reduced pressure with a nitrogen
  11. custompurge

出典と根拠

ORDレコード
ord-98ac96614dca4e70a07408ba36e83d82
出典データセット
uspto-grants-2003_08
特許番号
US06602868B2

反応ノート

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