Hydrochloric Acid → 6,7-Difluoro-2-methylquinoline

HRID 226256

反応式

HRID 226256 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl.[C:11]1(Cl)[C:17](=O)C(Cl)=C(Cl)[C:13](=O)[C:12]=1Cl.C(=O)/C=C/C>CC(O)CC.O>[F:9][C:8]1[CH:7]=[C:6]2[C:4](=[CH:3][C:2]=1[F:1])[N:5]=[C:12]([CH3:13])[CH:11]=[CH:17]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8371ChloranilHCID 774693,4-DifluoroanilineHCID 447466Crotonaldehyde

生成物 1

HCID 222413776,7-Difluoro-2-methylquinoline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6568(+-)-2-Butanol溶媒3 回

実験手順

25.0 g of 3,4-difluoroaniline are dissolved in 120 of 2-butanol. 50 ml of a saturated solution of hydrogen chloride in 2-butanol are added slowly and afterwards 47.6 g (0.1936 mol) of p-chloranil are also added. With a good stirring and at reflux temperature (100-110° C.) a solution of 19.4 ml (0.236 mol) of crotonaldehyde in 45 ml of butan-2-ol is dropped slowly (ca. 2 hr). The whole is refluxed for two additional hours and then evaporated to dryness. The residue is taken with excess THF and is filtered and washed thoroughly with THF until the filtering appears to be uncoloured. The solid thus obtained is solved in water, filtered from some solid impurities and washed with ethyl ether. The aqueous layer is made slightly alkaline with 2N NaOH solution and then extracted with diethyl ether. The ethereal layer is dried and treated with a little decolourising charcoal. After evaporation a white solid is obtained (22.7 g, 65%).

後処理

  1. additionis dropped slowly (ca. 2 hr)
  2. temperatureThe whole is refluxed for two additional hours
  3. customevaporated to dryness
  4. filtrationis filtered
  5. washwashed thoroughly with THF until the filtering
  6. customThe solid thus obtained
  7. filtrationfiltered from some solid impurities
  8. washwashed with ethyl ether
  9. extractionextracted with diethyl ether
  10. customThe ethereal layer is dried
  11. additiontreated with a little decolourising charcoal
  12. customAfter evaporation a white solid
  13. customis obtained (22.7 g, 65%)

出典と根拠

ORDレコード
ord-444fd3c357f94884b2f49eb41befdbd1
出典データセット
uspto-grants-2009_07
特許番号
US07557212B2

関連ノート

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