Acetic Acid → 6-methoxyquinoline-2-carboxylic Acid

HRID 1684537ノート

反応式

HRID 1684537 の反応式
Br.C([N:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12]C1C#N)(=O)C1C=CC=CC=1.N.[C:25]([OH:28])(=[O:27])[CH3:26]>O>[C:25]([C:26]1[CH:12]=[CH:13][C:14]2[C:19](=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[N:10]=1)([OH:28])=[O:27]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 260Hydrogen BromideHCID 2304931-benzoyl-6-methoxy-2H-quinoline-2-carbonitrile

生成物 1

HCID 111832986-methoxyquinoline-2-carboxylic Acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

270 ml of 48% hydrobromic acid are added to a solution of 217 g (0,747 mol) of 1-benzoyl-2-cyano-6-methoxy-1,2-dihydroquinoline in 270 ml of acetic acid, and the mixture is heated at reflux for 30 min. It is filtered and rinsed with diethyl ether, and the solid obtained is then suspended in 2 l of water and heated to 90° C. Aqueous ammonia is then added until the pH=8-9 and the mixture is filtered while hot. The filtrate is acidified at 50° C., by adding acetic acid until the pH=4-5, and is then cooled. The crystallized product is filtered off, rinsed with water and then recrystallized from 250 ml of acetic acid and rinsed with diethyl ether. 129 g of product are obtained.

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 30 min
  3. filtrationIt is filtered
  4. washrinsed with diethyl ether
  5. customthe solid obtained
  6. filtrationthe mixture is filtered while hot
  7. customis acidified at 50° C.
  8. additionby adding acetic acid until the pH=4-5
  9. temperatureis then cooled
  10. filtrationThe crystallized product is filtered off
  11. washrinsed with water
  12. customrecrystallized from 250 ml of acetic acid
  13. washrinsed with diethyl ether

出典と根拠

ORDレコード
ord-aba8c9286ee84709a12c6a2eb51a080d
出典データセット
uspto-grants-1997_06
特許番号
US05641785

反応ノート

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