Hydrochloric Acid → 2-Chloro-5-(3,4-dimethoxybenzoyl)pyridine

HRID 1031498ノート

反応式

HRID 1031498 の反応式
[Mg].Br[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.COC1C=C([Mg]Br)C=CC=1OC.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]=1.Cl>O1CCCC1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](=[O:31])[C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([O:11][CH3:12])[CH:4]=2)=[CH:28][N:27]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 27821656-Chloronicotinoyl ChlorideHCID 5462224MagnesiumHCID 178491916HCID 178491916、化合物

生成物 1

HCID 148232212-Chloro-5-(3,4-dimethoxybenzoyl)pyridine収率 67.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 200 ml of tetrahydrofuran were added metallic magnesium (5.35 g) and 4-bromoveratrole (47.8 g), and the mixture was heated for 3 hours under reflux to prepare a 3,4-dimethoxyphenyl magnesium bromide solution. This solution was added, while stirring, dropwise at temperatures ranging from -50° C. to -60° C. to a solution of 6-chloronicotinic acid chloride (21.2 g) in tetrahydrofuran (200 ml) (the time required for the addition: one hour). The resultant mixture was stirred at the same temperature for 2 hours and 40 minutes, and there was then added 2N hydrochloric acid (100 ml). Precipitating crystals were collected by filtration, washed with water and dried to afford 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine (22.5 g), m.p. 158° to 159° C.

後処理

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. additionThis solution was added
  4. additionrequired for the addition
  5. customone hour
  6. customPrecipitating crystals
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

出典と根拠

ORDレコード
ord-08caf5d4817b4389807aea87041433cf
出典データセット
uspto-grants-1990_09
特許番号
US04954497

反応ノート

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