Hydrochloric Acid → HCID 13567760、化合物

HRID 280190ノート

反応式

HRID 280190 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:14].[OH-].[K+].Cl>O1CCCC1.O.CO>[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:12]/[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:14])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 14797Potassium HydroxideHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehyde

生成物 1

HCID 13567760HCID 13567760、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6.5 g of 5-bromo-2-methoxypyridine-3-carboxaldehyde in 30 ml of tetrahydrofuran under nitrogen was added 200 ml of methanol followed by 4.6 g of 4-chloroacetophenone. Then, a solution of 6.6 g of 85% potassium hydroxide in 15 ml of water was added. The mixture warmed, became yellow, and deposited a thick precipitate. It was then stirred mechanically for about 1.5 hours until the temperature fell back to about 25° C. It was then further cooled in an ice bath and neutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions. The resulting pasty mixture was poured into 400 ml of water, acidified to a pH of 1 with aqueous 1N hydrochloric acid and then filtered. The moist product was boiled with 2-propanol/ethyl acetate (3:1), cooled and filtered. The filter cake was dried under reduced pressure to give (E)-3-(5-bromo-2-methoxy-3-pyridinyl)-1-(4-chlorophenyl)-2-propen-1-one as a pale yellow solid melting at about 168.5°-171.5° C.

後処理

  1. temperatureThe mixture warmed
  2. customfell back to about 25° C
  3. temperatureIt was then further cooled in an ice bath
  4. additionneutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions
  5. filtrationfiltered
  6. temperaturecooled
  7. filtrationfiltered
  8. customThe filter cake was dried under reduced pressure

出典と根拠

ORDレコード
ord-010e0abf979045488bd683666ec0d9a5
出典データセット
uspto-grants-1986_05
特許番号
US04588733

反応ノート

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